JP2009519277A - 3'-alkoxyspirocyclopentyl substituted tetramic acid and tetronic acid - Google Patents

Abstract

（Ｗ、Ｘ、Ｙ、Ｚ、Ａ、Ｂ、Ｄ、Ｑ^１、Ｑ^２およびＧは、明細書中示される意味を有する。）、この製造のための複数の方法および中間生成物、農薬および／または除草剤および／または殺真菌剤としてのこれらの使用、ならびに式（Ｉ）の３’−アルコキシスピロシクロペンチル−置換テトラミン酸およびテトロン酸および少なくとも１種の植物の耐性を改善する化合物を含む選択的除草剤に関する。さらに開示されるのは、アンモニウム塩および／またはホスホニウム塩を加えることにより、またはアンモニウム塩またはホスホニウム塩および浸透向上剤を加えることにより、式（Ｉ）の３’−アルコキシスピロシクロペンチル−置換テトラミン酸およびテトロン酸の類の薬剤を含有する作物保護製品の効果を増加させる方法、対応する薬剤、これらの製造法、ならびに作物保護でのこれらの使用である。The present invention relates to novel compounds of formula (I)

(W, X, Y, Z, A, B, D, Q ¹ , Q ² and G have the meanings indicated in the specification), multiple methods and intermediate products for this production, pesticides and And / or their use as herbicides and / or fungicides and selections comprising 3′-alkoxyspirocyclopentyl-substituted tetramic acids and tetronic acids of the formula (I) and compounds that improve the tolerance of at least one plant Related to herbicides. Further disclosed are 3′-alkoxyspirocyclopentyl-substituted tetramic acids of formula (I) and by adding ammonium and / or phosphonium salts or by adding ammonium or phosphonium salts and penetration enhancers. Methods for increasing the effectiveness of crop protection products containing drugs of the tetronic acid class, the corresponding drugs, their production, and their use in crop protection.

Description

  The present invention relates to novel 3'-alkoxyspirocyclopentyl substituted cyclic ketoenols, multiple processes for their preparation, and their use as insecticides, microbicides and / or herbicides. The present invention also provides a selective herbicidal composition comprising first a 3'-alkoxyspirocyclopentyl substituted cyclic ketoenol and secondly a crop suitability improving compound.

  The present invention further provides for the action of the corresponding composition through the addition of ammonium or phosphonium salts, and optionally penetrants, especially to crop protection compositions comprising 3'-alkoxyspirocyclopentyl substituted tetramic acid and tetronic acid. It relates to enhancing, the manufacturing process of these compositions, and the use of these compositions in crop protection as insecticides and / or acaricides and / or to prevent unwanted plant growth.

  1-H-arylpyrrolidinedione derivatives having a herbicidal, insecticidal or acaricidal action are known. EP-A-456063, EP-A-521334, EP-A-613384, EP-A-613858, WO95 / 01358, WO98 / 06721, WO98 / 25928, WO99 / 16748, WO99 / 24437, WO01 / 17972, WO05 / 044791, or WO05 / 048710.

  Also known are alkoxy-substituted spirocyclic 1H-arylpyrrolidinedione derivatives. EP-A-596298, WO95 / 26954, WO95 / 20572, EP-A-0668267, WO96 / 25395, WO96 / 35664, WO97 / 01535, WO97 / 02243, WO97 / 36868, WO98 / 05638, WO99 / 43649, WO99 / 48869, WO99 / 55673, WO01 / 23354, WO01 / 74770, WO01 / 17972, WO03 / 013249, WO04 / 024688, WO04 / 0665366, WO04 / 080962, WO04 / 007448, WO04 / 111042, WO05 / 044796, WO05 / 049569, WO05 / 066125, WO05 / 092897, WO06 / 000355, WO06 / 0297799, WO06 / 05628 , WO06 / 056282, WO06 / 089633.

Certain Δ ³ -dihydrofuran-2-one derivatives are known to have herbicidal, insecticidal or acaricidal properties. EP-A-528156, EP-A-647637, WO95 / 26954, WO96 / 20166, WO96 / 25395, WO96 / 35664, WO97 / 01535, WO97 / 02243, WO97 / 36868, WO98 / 05638, WO98 / 06721, WO99 / 16748, WO 98/25928, WO 99/43649, WO 99/48869, WO 99/55673, WO 01/23354, WO 01/74770, WO 01/17972, WO 2004/024688, WO 2004/080962, WO 04/111042, WO 05/092897, WO 06/000355, WO06 / 0297799, WO06 / 089633.

  However, the herbicidal and / or tick control and / or insecticidal activity and / or activity spectrum of known compounds and / or compatibility with plants, in particular crops, is not always sufficient.

  The present invention now provides the following formula (1):

式中
Ｗは水素、アルキル、アルケニル、アルキニル、ハロゲン、アルコキシ、ハロアルキル、ハロアルコキシまたはシアノを表し、
Ｘはハロゲン、アルキル、アルケニル、アルキニル、アルコキシ、アルコキシアルコキシ、ハロアルキル、ハロアルコキシまたはシアノを表し、
Ｙは水素、ハロゲン、アルキル、アルケニル、アルキニル、アルコキシ、シアノ、ハロアルキル、ハロアルコキシを表し、それぞれ場合により置換されたフェニルまたはヘタリールを表し、
Ｚは水素、ハロゲン、アルキル、ハロアルキル、シアノ、アルコキシまたはハロアルコキシを表し、
Ａは場合により置換されたアルカンジイル基を表し、またはシクロアルキル（ヘテロ原子で場合により置換および／または場合により中断される。）を表し、
Ｂは水素またはそれぞれ場合により置換されたアルキル、アルケニル、アルコキシ、アルコキシアルコキシ、フェニル、ヘタリールを表し、シクロアルキル（ヘテロ原子および／またはＣ＝Ｏで場合により置換および／または場合により中断される。）を表し、
またはＡは結合を表してＢは水素を表し、
ＤはＮＨまたは酸素を表し、
Ｑ^１は水素を表し、それぞれ場合により置換されたアルキル、アルコキシ、アルコキシアルキルまたはアルキルチオアルキルを表し、それぞれ場合により置換されたシクロアルキル（場合により１つのメチレン基がヘテロ原子で置換される。）を表し、または場合により置換されたフェニル、ヘタリール、フェニルアルキルまたはヘタリールアルキルを表し、
Ｑ^２は水素またはアルキルを表し、
Ｑ^１およびＱ^２は、これらが結合した炭素と一緒になって、場合により置換されたＣ_３−Ｃ_６−環（場合によりヘテロ原子で中断されてもよい。）を表し、または
Ｑ^１およびＱ^２は、これらが結合した炭素原子と一緒になって、場合により置換されたＣ_３−Ｃ_６−環（場合によりヘテロ原子で中断されてもよい。）を表し、
Ｇは水素（ａ）を表し、または以下の基のうち１つを表し、

In which W represents hydrogen, alkyl, alkenyl, alkynyl, halogen, alkoxy, haloalkyl, haloalkoxy or cyano;
X represents halogen, alkyl, alkenyl, alkynyl, alkoxy, alkoxyalkoxy, haloalkyl, haloalkoxy or cyano,
Y represents hydrogen, halogen, alkyl, alkenyl, alkynyl, alkoxy, cyano, haloalkyl, haloalkoxy, each optionally substituted phenyl or hetaryl;
Z represents hydrogen, halogen, alkyl, haloalkyl, cyano, alkoxy or haloalkoxy,
A represents an optionally substituted alkanediyl group or cycloalkyl (optionally substituted and / or optionally interrupted with a heteroatom);
B represents hydrogen or optionally substituted alkyl, alkenyl, alkoxy, alkoxyalkoxy, phenyl, hetaryl, cycloalkyl (heteroatom and / or optionally substituted and / or optionally interrupted with C═O). Represents
Or A represents a bond and B represents hydrogen;
D represents NH or oxygen,
Q ¹ represents hydrogen, each optionally substituted alkyl, alkoxy, alkoxyalkyl or alkylthioalkyl, each optionally substituted cycloalkyl (optionally one methylene group is replaced by a heteroatom). Represents, or optionally substituted phenyl, hetaryl, phenylalkyl or hetarylalkyl;
Q ² represents hydrogen or alkyl,
Q ¹ and Q ² together with the carbon to which they are attached represent an optionally substituted C ₃ -C ₆ -ring (optionally interrupted by a heteroatom), or Q ¹ and Q ² together with the carbon atom to which they are attached represents an optionally substituted C ₃ -C ₆ -ring (optionally interrupted by a heteroatom);
G represents hydrogen (a), or one of the following groups:

Ｅは金属イオンまたはアンモニウムイオンを表し、
Ｌは酸素または硫黄を表し、
Ｍは酸素または硫黄を表し、
Ｒ^１はそれぞれ場合によりハロゲンまたはシアノで置換されたアルキル、アルケニル、アルコキシアルキル、アルキルチオアルキルまたはポリアルコキシアルキルを表し、またはそれぞれ場合によりハロゲン、アルキルまたはアルコキシで置換されたシクロアルキルまたはヘテロシクリルを表し、またはそれぞれ場合により置換されたフェニル、フェニルアルキル、ヘタリール、フェノキシアルキルまたはヘタリールオキシアルキルを表し、
Ｒ^２はそれぞれ場合によりハロゲンまたはシアノで置換されたアルキル、アルケニル、アルコキシアルキルまたはポリアルコキシアルキルを表し、またはそれぞれ場合により置換されたシクロアルキル、フェニルまたはベンジルを表し、
Ｒ^３、Ｒ^４およびＲ^５は、互いに独立して、それぞれ場合によりハロゲンで置換されたアルキル、アルコキシ、アルキルアミノ、ジアルキルアミノ、アルキルチオ、アルケニルチオまたはシクロアルキルチオを表し、またはそれぞれ場合により置換されたフェニル、ベンジル、フェノキシまたはフェニルチオを表し、
Ｒ^６およびＲ^７は、互いに独立して、水素を表し、それぞれ場合によりハロゲンまたはシアノで置換されたアルキル、シクロアルキル、アルケニル、アルコキシ、アルコキシアルキルを表し、それぞれ場合により置換されたフェニルまたはベンジルを表し、またはこれらが結合したＮ原子と一緒になって場合により置換された環（場合により酸素または硫黄を含有する。）を形成する、
の新規化合物を提供する。

E represents a metal ion or an ammonium ion;
L represents oxygen or sulfur;
M represents oxygen or sulfur,
R ¹ represents alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl or polyalkoxyalkyl, each optionally substituted with halogen or cyano, or each represents cycloalkyl or heterocyclyl optionally substituted with halogen, alkyl or alkoxy, or Each represents optionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl;
R ² represents alkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl, each optionally substituted with halogen or cyano, or each independently represents cycloalkyl, phenyl or benzyl,
R ³ , R ⁴ and R ⁵ independently of one another each represent alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio or cycloalkylthio, each optionally substituted with halogen, or each optionally substituted Represents phenyl, benzyl, phenoxy or phenylthio;
R ⁶ and R ⁷ independently of one another represent hydrogen, each representing alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl optionally substituted with halogen or cyano, each independently substituted phenyl or benzyl Together with the N atom to which they are attached to form an optionally substituted ring (optionally containing oxygen or sulfur),
The novel compounds are provided.

  Depending on, inter alia, the nature of the substituents, the compounds of formula (I) may exist as optical isomers or as a mixture of various isomers of composition, which isomer mixtures, if appropriate, in the usual manner. It may be separated. The present invention provides pure isomers and mixtures of isomers, their preparation and use, and compositions comprising them. For the sake of simplicity, only the compounds of the formula (I) are shown below, but not only pure compounds but also mixtures containing various proportions of isomeric compounds where appropriate.

  When D is NH (1) and D is O (2), the following main structures (I-1) to (I-2) are obtained.

ここで、
Ａ、Ｂ、Ｇ、Ｑ^１、Ｑ^２、Ｗ、Ｘ、ＹおよびＺは、上記で定義されるとおりである。

here,
A, B, G, Q ¹ , Q ² , W, X, Y and Z are as defined above.

  Including (a), (b), (c), (d), (e), (f) and (g), respectively, when the group G means, if D represents NH (1), then (I-1-g) is obtained from the main structure (I-1-a).

式中、
Ａ、Ｂ、Ｅ、Ｌ、Ｍ、Ｑ^１、Ｑ^２、Ｗ、Ｘ、Ｙ、Ｚ、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５、Ｒ^６、およびＲ^７は、上記で定義されるとおりである。

Where
A, B, E, L, M, Q ¹ , Q ² , W, X, Y, Z, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , and R ⁷ are defined above. It is as it is done.

  Including (a), (b), (c), (d), (e), (f) and (g), respectively, when the group G means, if D represents O (2), then (I-2-g) is obtained from the main structure (I-2-a)

式中、
Ａ、Ｂ、Ｅ、Ｌ、Ｍ、Ｑ^１、Ｑ^２、Ｗ、Ｘ、Ｙ、Ｚ、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５、Ｒ６およびＲ７は、上記で定義されるとおりである。

Where
A, B, E, L, M, Q ¹ , Q ² , W, X, Y, Z, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R6 and R7 are as defined above. It is.

Furthermore, it has been found that the novel compounds of formula (I) are obtained by the process described below:
(A) Compound of formula (I-1-a)

式中、
Ａ、Ｂ、Ｑ^１、Ｑ^２、Ｗ、Ｘ、ＹおよびＺは、上記で定義されるとおりである、
は、希釈剤の存在下、および塩基の存在下で、
式（ＩＩ）の化合物

Where
A, B, Q ¹ , Q ² , W, X, Y and Z are as defined above,
In the presence of diluent and in the presence of a base,
Compound of formula (II)

式中、
Ａ、Ｂ、Ｑ^１、Ｑ^２、Ｗ、Ｘ、ＹおよびＺは、上記で定義されるとおりであり、
Ｒ^８は、アルキル（好ましくはＣ_１−Ｃ_６−アルキル）を表し、
を、分子内縮合させると得られる。
（Ｂ）さらに、式（Ｉ−２−ａ）の化合物

Where
A, B, Q ¹ , Q ² , W, X, Y and Z are as defined above,
R ⁸ represents alkyl (preferably C ₁ -C ₆ -alkyl);
Is obtained by intramolecular condensation.
(B) Further, a compound of formula (I-2-a)

式中、
Ａ、Ｂ、Ｑ^１、Ｑ^２、Ｗ、Ｘ、ＹおよびＺは、上記で定義されるとおりである、
は、希釈剤の存在下、および塩基の存在下で、
式（ＩＩＩ）の化合物

Where
A, B, Q ¹ , Q ² , W, X, Y and Z are as defined above,
In the presence of diluent and in the presence of a base,
Compound of formula (III)

式中、
Ａ、Ｂ、Ｑ^１、Ｑ^２、Ｗ、Ｘ、Ｙ、ＺおよびＲ^８は、上記で定義されるとおりである、
を、分子内縮合させると得られることが見いだされた。

Where
A, B, Q ¹ , Q ² , W, X, Y, Z and R ⁸ are as defined above.
Was found to be obtained by intramolecular condensation.

In addition, the following was found:
(C) Compounds of formula (I-1-b) to (I-2-b) above (R ¹ , A, B, Q ¹ , Q ² , W, X, Y and Z are defined above. Is a compound of the above formulas (I-1-a) to (I-2-a), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder. (A, B, Q ¹ , Q ² , W, X, Y and Z are as defined above), respectively,
α) Compound of formula (IV)

式中、
Ｒ^１は上記で定義されるとおりであり、
Ｈａｌはハロゲンを表し、
または、
β）式（Ｖ）の無水カルボン酸
Ｒ^１−ＣＯ−Ｏ−ＣＯ−Ｒ^１（Ｖ）
式中、
Ｒ^１は上記で定義されるとおりである、
と反応させた場合に得られる；
（Ｄ）上記の式（Ｉ−１−ｃ）から（Ｉ−２−ｃ）の化合物（Ｒ^２、Ａ、Ｂ、Ｑ^１、Ｑ^２、Ｗ、Ｍ、Ｘ、ＹおよびＺは、上記で定義されるとおりであり、Ｌは酸素を表す）は、適切ならば希釈剤の存在下で、および適切ならば酸結合剤の存在下で、上記の式（Ｉ−１−ａ）から（Ｉ−２−ａ）の化合物（Ａ、Ｂ、Ｑ^１、Ｑ^２、Ｗ、Ｘ、ＹおよびＺは、上記で定義されるとおりである。）を、それぞれ、以下の式（ＶＩ）
Ｒ^２−Ｍ−ＣＯ−Ｃｌ（ＶＩ）
式中、
Ｒ^２およびＭは、上記で定義されるとおりである
のクロロギ酸エステルまたはクロロギ酸チオエステルと反応させた場合に得られる；
（Ｅ）上記の式（Ｉ−１−ｃ）から（Ｉ−２−ｃ）の化合物（Ｒ^２、Ａ、Ｂ、Ｑ^１、Ｑ^２、Ｗ、Ｍ、Ｘ、ＹおよびＺは、上記で定義されるとおりであり、Ｌは硫黄を表す）は、適切ならば希釈剤の存在下で、および適切ならば酸結合剤の存在下で、上記の式（Ｉ−１−ａ）から（Ｉ−２−ａ）の化合物（Ａ、Ｂ、Ｑ^１、Ｑ^２、Ｗ、Ｘ、ＹおよびＺは、上記で定義されるとおりである。）を、それぞれ、以下の式（ＶＩＩ）

Where
R ¹ is as defined above,
Hal represents halogen,
Or
β) Carboxylic anhydride of formula (V) R ¹ —CO—O—CO—R ¹ (V)
Where
R ¹ is as defined above,
Obtained when reacted with
(D) The compounds of the above formulas (I-1-c) to (I-2-c) (R ² , A, B, Q ¹ , Q ² , W, M, X, Y and Z are As defined and L represents oxygen) in the presence of a diluent, if appropriate, and in the presence of an acid binder, if appropriate, from formula (I-1-a) above (I 2-a) compounds (A, B, Q ¹ , Q ² , W, X, Y and Z are as defined above), each of the following formula (VI):
^{R 2 -M-CO-Cl (} VI)
Where
R ² and M are obtained when reacted with a chloroformate or chloroformate thioester as defined above;
(E) Compounds of formulas (I-1-c) to (I-2-c) above (R ² , A, B, Q ¹ , Q ² , W, M, X, Y and Z are As defined and L represents sulfur, if appropriate in the presence of a diluent and, where appropriate, in the presence of an acid binder, from formula (I-1-a) above (I 2-a) compounds (A, B, Q ¹ , Q ² , W, X, Y and Z are as defined above), each of the following formula (VII)

式中、
ＭおよびＲ^２は、上記で定義されるとおりである、
のクロロモノチオギ酸エステルまたはクロロジチオギ酸エステルと反応させた場合に得られる、
（Ｆ）上記の式（Ｉ−１−ｄ）から（Ｉ−２−ｄ）の化合物（Ｒ^３、Ａ、Ｂ、Ｗ、Ｑ^１、Ｑ^２、Ｘ、ＹおよびＺは、上記で定義されるとおりである。）は、適切ならば希釈剤の存在下で、および適切ならば酸結合剤の存在下で、上記の式（Ｉ−１−ａ）から（Ｉ−２−ａ）の化合物（Ａ、Ｂ、Ｑ^１、Ｑ^２、Ｗ、Ｘ、ＹおよびＺは、上記で定義されるとおりである。）を、それぞれ、以下の式（ＶＩＩＩ）
Ｒ^３−ＳＯ_２−Ｃｌ（ＶＩＩＩ）
式中、
Ｒ^３は上記で定義されるとおりである、
のスルホニルクロリドと反応させた場合に得られる、
（Ｇ）上記の式（Ｉ−１−ｅ）から（Ｉ−２−ｅ）の化合物（Ｌ、Ｒ^４、Ｒ^５、Ａ、Ｂ、Ｑ^１、Ｑ^２、Ｗ、Ｘ、ＹおよびＺは、上記で定義されるとおりである。）は、適切ならば希釈剤の存在下で、および適切ならば酸結合剤の存在下で、上記の式（Ｉ−１−ａ）から（Ｉ−２−ａ）の化合物（Ａ、Ｂ、Ｑ^１、Ｑ^２、Ｗ、Ｘ、ＹおよびＺは、上記で定義されるとおりである。）を、それぞれ、以下の式（ＩＸ）

Where
M and R ² are as defined above.
Obtained by reacting with chloromonothioformate or chlorodithioformate,
(F) Compounds of formula (I-1-d) to (I-2-d) above (R ³ , A, B, W, Q ¹ , Q ² , X, Y and Z are defined above. Is a compound of the above formulas (I-1-a) to (I-2-a), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder. (A, B, Q ¹ , Q ² , W, X, Y and Z are as defined above), respectively, in the following formula (VIII)
R ³ —SO ₂ —Cl (VIII)
Where
R ³ is as defined above,
Obtained by reacting with sulfonyl chloride of
(G) Compounds (L, R ⁴ , R ⁵ , A, B, Q ¹ , Q ² , W, X, Y, and Z of the above formulas (I-1-e) to (I-2-e) are As defined above) in the presence of a diluent, if appropriate, and in the presence of an acid binder, if appropriate, from formulas (I-1-a) to (I-2) -A) compounds (A, B, Q ¹ , Q ² , W, X, Y and Z are as defined above), each of the following formula (IX):

式中、
Ｌ、Ｒ^４、およびＲ^５は、上記で定義されるとおりであり、
Ｈａｌはハロゲン（特に塩素または臭素）を表し、
のリン化合物と反応させた場合に得られる、
（Ｈ）上記の式（Ｉ−１−ｆ）から（Ｉ−２−ｆ）の化合物（Ｅ、Ａ、Ｂ、Ｑ^１、Ｑ^２、Ｗ、Ｘ、ＹおよびＺは、上記で定義されるとおりである。）は、適切ならば希釈剤の存在下で、上記の式（Ｉ−１−ａ）から（Ｉ−２−ａ）の化合物（Ａ、Ｂ、Ｑ^１、Ｑ^２、Ｗ、Ｘ、ＹおよびＺは、上記で定義されるとおりである。）を、それぞれ、以下のそれぞれ式（Ｘ）および（ＸＩ）
Ｍｅ（ＯＲ^１０）_ｔ（Ｘ）

Where
L, R ⁴ , and R ⁵ are as defined above,
Hal represents halogen (especially chlorine or bromine)
Obtained when reacted with a phosphorus compound of
(H) Compounds of formula (I-1-f) to (I-2-f) above (E, A, B, Q ¹ , Q ² , W, X, Y and Z are defined above. In the presence of diluent, if appropriate, of the compounds of formulas (I-1-a) to (I-2-a) (A, B, Q ¹ , Q ² , W, X, Y and Z are as defined above), respectively, in the following formulas (X) and (XI) respectively:
Me (OR ¹⁰ ) _t (X)

式中、
Ｍｅは１価または２価金属（好ましくは、アルカリ金属またはアルカリ土類金属、例えばリチウム、ナトリウム、カリウム、マグネシウム、またはカルシウムなど）を表し、
ｔは１または２の数値を表し、
Ｒ^１０、Ｒ^１１、Ｒ^１２は、互いに独立して、水素またはアルキル（好ましくはＣ_１−Ｃ_８−アルキル）を表し、
の金属化合物またはアミンと反応させた場合に得られる、
（Ｉ）上記の式（Ｉ−１−ｇ）から（Ｉ−２−ｇ）の化合物（Ｌ、Ｒ^６、Ｒ^７、Ａ、Ｂ、Ｑ^１、Ｑ^２、Ｗ、Ｘ、ＹおよびＺは、上記で定義されるとおりである。）は、上記の式（Ｉ−１−ａ）から（Ｉ−２−ａ）の化合物（Ａ、Ｂ、Ｑ^１、Ｑ^２、Ｗ、Ｘ、ＹおよびＺは、上記で定義されるとおりである。）を、それぞれ、
α）適切ならば希釈剤の存在下で、および適切ならば触媒の存在下で、以下の式（ＸＩＩ）
Ｒ^６−Ｎ＝Ｃ＝Ｌ（ＸＩＩ）
式中、
Ｒ^６およびＬは上記で定義されるとおりである、
のイソシアナートまたはイソチオシアナートと反応させ、または
β）適切ならば希釈剤の存在下で、および適切ならば酸結合剤の存在下で、以下の式（ＸＩＩＩ）

Where
Me represents a monovalent or divalent metal (preferably an alkali metal or alkaline earth metal such as lithium, sodium, potassium, magnesium or calcium),
t represents a numerical value of 1 or 2,
R ¹⁰ , R ¹¹ , R ¹² independently of one another represent hydrogen or alkyl (preferably C ₁ -C ₈ -alkyl);
Obtained when reacted with a metal compound or amine of
(I) Compounds (L, R ⁶ , R ⁷ , A, B, Q ¹ , Q ² , W, X, Y, and Z of the above formulas (I-1-g) to (I-2-g) are As defined above) is a compound of formulas (I-1-a) to (I-2-a) (A, B, Q ¹ , Q ² , W, X, Y and Z is as defined above.)
α) in the presence of a diluent, if appropriate, and in the presence of a catalyst, if appropriate, of formula (XII)
^{R 6 -N = C = L (} XII)
Where
R ⁶ and L are as defined above.
Or β) if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder, the following formula (XIII)

式中、
Ｌ、Ｒ^６およびＲ^７は、上記で定義されるとおりである、
のカルバモイルクロリドまたはチオカルバモイルクロリドと反応させた場合に得られる。

Where
L, R ⁶ and R ⁷ are as defined above,
Obtained by reacting with carbamoyl chloride or thiocarbamoyl chloride.

  Furthermore, the novel compounds of formula (1) are very effective as agricultural chemicals, preferably as insecticides, acaricides and / or fungicides and / or herbicides, and plants, in particular crops, It has been found that it is often very well tolerated.

  Surprisingly, when certain substituted cyclic ketoenols are used in conjunction with the crop compatibility-improving compounds described below (safeners / antidote), the substituted cyclic ketoenols effectively damage the crop. Particularly advantageous as a broad-spectrum combination preparation for the selective control of unwanted plants in crops of useful plants, for example in cereals and also in corn, soybeans and rice It has also been found here that it can be used in a style.

The present invention also includes, as a constituent, the following (a ′) at least one compound of formula (I) (A, B, D, G, Q ¹ , Q ² , W, X, Y and Z And (b ′) at least one crop suitability improving compound from the group of the following compounds:
4-dichloroacetyl-1-oxa-4-azaspiro [4.5] decane (AD-67, MON-4660), 1-dichloroacetylhexahydro-3,3,8a-trimethylpyrrolo [1,2-a] Pyrimidin-6 (2H) -one (dicyclonone, BAS-145138), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (benoxacol), 1-methylhexyl -Chloroquinoline-8-oxyacetate (Croquintoset mexil-note, EP-A-86750, EP-A-94349, EP-A-191736, EP-A-492366 and related compounds), 3- ( 2-Chlorobenzyl) -1- (1-methyl-1-phenylethyl) urea (cumyluron), α- (cyanomethoxyimino) phenyl Cetonitrile (Siomethrinyl), 2,4-Dichlorophenoxyacetic acid (2,4-D), 4- (2,4-Dichlorophenoxy) butyric acid (2,4-DB), 1- (1-Methyl-1-phenylethyl) ) -3- (4-Methylphenyl) urea (Dimron), 3,6-dichloro-2-methoxybenzoic acid (dicamba), S-1-methyl-1-phenylethylpiperidine-1-thiocarboxylate (dimethylpiperate) 2,2-dichloro-N- (2-oxo-2- (2-propenylamino) ethyl) -N- (2-propenyl) acetamide (DKA-24), 2,2-dichloro-N, N-di -2-propenylacetamide (dichloroimide), 4,6-dichloro-2-phenylpyrimidine (phenchlorim), ethyl 1- (2,4-dichlorophenyl) -5 Trichloromethyl-1H-1,2,4-triazole-3-carboxylate (phenchlorazole ethyl-note, EP-A-174562 and EP-A-346620 and related compounds), phenylmethyl 2-chloro-4- Trifluoromethylthiazole-5-carboxylate (flurazole), 4-chloro-N- (1,3-dioxolan-2-ylmethoxy) -α-trifluoroacetophenone oxime (fluxophenim), 3-dichloroacetyl-5- (2 -Furanyl) -2,2-dimethyloxazolidine (Frilazole, MON-13900), ethyl 4,5-dihydro-5,5-diphenyl-3-ioxazolecarboxylate (Ioxadiphenethyl-Note, WO-A- 95/07897 also related compounds), 1- (ethoxy Rubonyl) ethyl 3,6-dichloro-2-methoxybenzoate (lactide dichloro), (4-chloro-o-toluyloxy) acetic acid (MCPA), 2- (4-chloro-o-toluyloxy) propionic acid (mecoprop) Diethyl 1- (2,4-dichlorophenyl) -4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate (mefenpyr diethyl-note, also in WO-A-91 / 07874) Related compounds), 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191), 2-propenyl-1-oxa-4-azaspiro [4.5] decane-4-carbodithioate (MG-) 838), 1,8-naphthalic anhydride, α- (1,3-dioxolan-2-ylmethoxyimino) phenylacetonitrile (oxabeto Linyl), 2,2-dichloro-N- (1,3-dioxolan-2-ylmethyl) -N- (2-propenyl) acetamide (PPG-1292), 3-dichloroacetyl-2,2-dimethyloxazolidine (R -28725), 3-dichloroacetyl-2,2,5-trimethyloxazolidine (R-29148), 4- (4-chloro-o-toluyl) butyric acid, 4- (4-chlorophenoxy) butyric acid, diphenylmethoxyacetic acid, Methyldiphenylmethoxyacetate, ethyldiphenylmethoxyacetate, methyl 1- (2-chlorophenyl) -5-phenyl-1H-pyrazole-3-carboxylate, ethyl 1- (2,4-dichlorophenyl) -5-methyl-1H -Pyrazole-3-carboxylate, ethyl 1- (2,4-dichlorophenyl) 5-isopropyl-1H-pyrazole-3-carboxylate, ethyl 1- (2,4-dichlorophenyl) -5- (1,1-dimethylethyl) -1H-pyrazole-3-carboxylate, ethyl 1- (2, 4-dichlorophenyl) -5-phenyl-1H-pyrazole-3-carboxylate (note, also related to EP-A-269806 and EP-A-333131), ethyl 5- (2,4-dichlorobenzyl) -2 -Ixazoline-3-carboxylate, ethyl 5-phenyl-2-ixazoline-3-carboxylate, ethyl 5- (4-fluorophenyl) -5-phenyl-2-oxazoline-3-carboxylate (note, WO-A-91 / 08202 is also a related compound), 1,3-dimethylbut-1-yl 5-chloroalkyl Phosphorus-8-oxyacetate, 4-allyloxybutyl 5-chloroquinoline-8-oxyacetate, 1-allyloxyprop-2-yl 5-chloroquinoline-8-oxyacetate, methyl 5-chloroquinoxaline- 8-oxyacetate, ethyl 5-chloroquinoline-8-oxyacetate, allyl 5-chloroquinoxaline-8-oxyacetate, 2-oxoprop-1-yl 5-chloroquinoline-8-oxyacetate, diethyl 5 -Chloroquinoline-8-oxymalonate, diallyl 5-chloroquinoxaline-8-oxymalonate, diethyl 5-chloroquinoline-8-oxymalonate (Note, also related to EP-A-582198), 4-carboxy Chroman-4-ylacetic acid (AC-304415, Note, EP-A-6 3618), 4-chlorophenoxyacetic acid, 3,3′-dimethyl-4-methoxybenzophenone, 1-bromo-4-chloromethylsulfonylbenzene, 1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea (N- (2-methoxybenzoyl) -4-[(methylaminocarbonyl) amino] benzenesulfonamide), 1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl ] -3,3-dimethylurea, 1- [4- (N-4,5-dimethylbenzoylsulfamoyl) phenyl] -3-methylurea, 1- [4- (N-naphthylsulfamoyl) phenyl] -3,3-dimethylurea, N- (2-methoxy-5-methylbenzoyl) -4- (cyclopropylaminocarbonyl) benzenes Hon'amido,
And / or the following formula (IIa)

または式（ＩＩｂ）

Or formula (IIb)

または式（ＩＩｃ）

Or formula (IIc)

ここで
ｍは、０、１、２、３、４または５の数値を表し、
Ａ^１は、以下に示す２価ヘテロ環式基のうち１つを表し、

Here, m represents a numerical value of 0, 1, 2, 3, 4 or 5,
A ¹ represents one of the divalent heterocyclic groups shown below,

ｎは、０、１、２、３、４または５の数値を表し、
Ａ^２は、場合によりＣ１−Ｃ４−アルキルおよび／またはＣ１−Ｃ４−アルコキシカルボニルおよび／またはＣ１−Ｃ４−アルケニルオキシカルボニルで置換された、１個または２個の炭素原子を有するアルカンジイルを表し、
Ｒ^１４は、ヒドロキシル、メルカプト、アミノ、Ｃ_１−Ｃ_６−アルコキシ、Ｃ_１−Ｃ_６−アルキルチオ、Ｃ_１−Ｃ_６−アルキルアミノまたはジ（Ｃ_１−Ｃ_４−アルキル）−アミノを表し、
Ｒ^１５は、ヒドロキシル、メルカプト、アミノ、Ｃ_１−Ｃ_７−アルコキシ、Ｃ_１−Ｃ_６−アルケニルオキシ、Ｃ_１−Ｃ_６−アルケニルオキシ−Ｃ_１−Ｃ_６−アルコキシ、Ｃ_１−Ｃ_６−アルキルチオ、Ｃ_１−Ｃ_６−アルキルアミノまたはジ（Ｃ_１−Ｃ_４−アルキル）−アミノを表し、
Ｒ^１６は、場合によりフッ素、塩素および／または臭素で置換されたＣ_１−Ｃ_４−アルキルを表し、
Ｒ^１７は、水素、それぞれ場合によりフッ素、塩素および／または臭素で置換されたＣ_１−Ｃ_６−アルキル、Ｃ_２−Ｃ_６−アルケニルもしくはＣ_２−Ｃ_６−アルキニル、Ｃ_１−Ｃ_４−アルコキシ−Ｃ_１−Ｃ_４−アルキル、ジオキソラニル−Ｃ_１−Ｃ_４−アルキル、フリル、フリル−Ｃ_１−Ｃ_４−アルキル、チエニル、チアゾリル、ピペリジニル、または場合によりフッ素、塩素および／または臭素で、またはＣ_１−Ｃ_４−アルキルで置換されたフェニルを表し、
Ｒ^１８は、水素、それぞれ場合によりフッ素、塩素および／または臭素で置換されたＣ_１−Ｃ_６−アルキル、Ｃ_２−Ｃ_６−アルケニルもしくはＣ_２−Ｃ_６−アルキニル、Ｃ_１−Ｃ_４−アルコキシ−Ｃ_１−Ｃ_４−アルキル、ジオキソラニル−Ｃ_１−Ｃ_４−アルキル、フリル、フリル−Ｃ_１−Ｃ_４−アルキル、チエニル、チアゾリル、ピペリジニル、または場合によりフッ素、塩素および／または臭素で、またはＣ_１−Ｃ_４−アルキルで置換されたフェニルを表し、Ｒ^１７とＲ^１８は、一緒になって、Ｃ_３−Ｃ_６−アルカンジイルまたはＣ_２−Ｃ_５−オキサアルカンジイルを表し（それぞれ場合によりＣ_１−Ｃ_４−アルキル、フェニル、フリル、縮環したベンゼン環で置換され、２つの置換基で置換されて２つの置換基はこれらが結合したＣ原子と一緒に５員または６員炭素環を形成する。）、
Ｒ^１９は、水素、シアノ、ハロゲンを表し、それぞれ場合によりフッ素、塩素および／または臭素で置換されたＣ_１−Ｃ_４−アルキル、Ｃ_３−Ｃ_６−シクロアルキルまたはフェニルを表し、
Ｒ^２０は、水素、それぞれ場合によりヒドロキシル、シアノ、ハロゲンまたはＣ１−Ｃ４−アルコキシで置換されたＣ_１−Ｃ_６−アルキル、Ｃ_３−Ｃ_６−シクロアルキルまたはトリ−（Ｃ_１−Ｃ_４−アルキル）−シリルを表し、
Ｒ^２１は、水素、シアノ、ハロゲンを表し、またはそれぞれ場合によりフッ素、塩素および／または臭素で置換されたＣ_１−Ｃ_４−アルキル、Ｃ_３−Ｃ_６−シクロアルキルまたはフェニルを表し、
Ｘ^１は、ニトロ、シアノ、ハロゲン、Ｃ_１−Ｃ_４−アルキル、Ｃ_１−Ｃ_４−ハロアルキル、Ｃ_１−Ｃ_４−アルコキシまたはＣ_１−Ｃ_４−ハロアルコキシを表し、
Ｘ^２は、水素、シアノ、ニトロ、ハロゲン、Ｃ_１−Ｃ_４−アルキル、Ｃ_１−Ｃ_４−ハロアルキル、Ｃ_１−Ｃ_４−アルコキシまたはＣ_１−Ｃ_４−ハロアルコキシを表し、
Ｘ^３は、水素、シアノ、ニトロ、ハロゲン、Ｃ_１−Ｃ_４−アルキル、Ｃ_１−Ｃ_４−ハロアルキル、Ｃ_１−Ｃ_４−アルコキシまたはＣ_１−Ｃ_４−ハロアルコキシを表し、
の一般式で定義される化合物のうちの１つ、
および／または以下
式（ＩＩｄ）

n represents a numerical value of 0, 1, 2, 3, 4 or 5;
A ² represents alkanediyl having 1 or 2 carbon atoms, optionally substituted with C1-C4-alkyl and / or C1-C4-alkoxycarbonyl and / or C1-C4-alkenyloxycarbonyl;
R ¹⁴ represents hydroxyl, mercapto, amino, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkylthio, C ₁ -C ₆ -alkylamino or di (C ₁ -C ₄ -alkyl) -amino;
R ¹⁵ is hydroxyl, mercapto, amino, C ₁ -C ₇ -alkoxy, C ₁ -C ₆ -alkenyloxy, C ₁ -C ₆ -alkenyloxy-C ₁ -C ₆ -alkoxy, C ₁ -C _{6- alkylthio,} C 1 -C ₆ - alkylamino or di _(C 1 -C ₄ - alkyl) - an amino,
R ¹⁶ represents C ₁ -C ₄ -alkyl optionally substituted with fluorine, chlorine and / or bromine;
R ¹⁷ is hydrogen, fluorine, optionally respectively, chlorine and / or _C 1 -C bromine-substituted ₆ - _alkyl, C 2 -C ₆ - alkenyl or _C 2 -C ₆ - _alkynyl, C 1 -C ₄ - Alkoxy-C ₁ -C ₄ -alkyl, dioxolanyl-C ₁ -C ₄ -alkyl, furyl, furyl-C ₁ -C ₄ -alkyl, thienyl, thiazolyl, piperidinyl, or optionally fluorine, chlorine and / or bromine, Or represents phenyl substituted with C ₁ -C ₄ -alkyl,
R ¹⁸ is hydrogen, fluorine, optionally respectively, _C 1 -C substituted by chlorine and / or bromine ₆ - _alkyl, C 2 -C ₆ - alkenyl or _C 2 -C ₆ - _alkynyl, C 1 -C ₄ - Alkoxy-C ₁ -C ₄ -alkyl, dioxolanyl-C ₁ -C ₄ -alkyl, furyl, furyl-C ₁ -C ₄ -alkyl, thienyl, thiazolyl, piperidinyl, or optionally fluorine, chlorine and / or bromine, Or phenyl substituted with C ₁ -C ₄ -alkyl, R ¹⁷ and R ^{18 taken} together represent C ₃ -C ₆ -alkanediyl or C ₂ -C ₅ -oxaalkanediyl (respectively optionally C ₁ -C 4 _- alkyl, phenyl, furyl, substituted with condensed benzene rings, two substituted with two substituents Substituents form a 5-membered or 6-membered carbocyclic ring together with the C atom to which they are attached.)
R ¹⁹ represents hydrogen, cyano, halogen, each representing C ₁ -C ₄ -alkyl, C ₃ -C ₆ -cycloalkyl or phenyl optionally substituted with fluorine, chlorine and / or bromine,
R ²⁰ is hydrogen, optionally substituted by hydroxyl, respectively, cyano, _C 1 -C substituted by halogen or C1-C4- alkoxy ₆ - _alkyl, C 3 -C ₆ - cycloalkyl or tri - _(C 1 -C ₄ - Alkyl) -silyl,
R ²¹ represents hydrogen, cyano, halogen, or C ₁ -C ₄ -alkyl, C ₃ -C ₆ -cycloalkyl or phenyl, each optionally substituted with fluorine, chlorine and / or bromine,
X ¹ represents nitro, cyano, halogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -haloalkoxy,
X ² represents hydrogen, cyano, nitro, halogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -haloalkoxy,
X ³ represents hydrogen, cyano, nitro, halogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -haloalkoxy,
One of the compounds defined by the general formula:
And / or the following formula (IId)

または式（ＩＩｅ）

Or formula (IIe)

ここで、
ｔは、０、１、２、３、４または５の数値を表し、
ｖは、０、１、２、３、４または５の数値を表し、
Ｒ^２２は、水素またはＣ_１−Ｃ_４−アルキルを表し、
Ｒ^２３は、水素またはＣ_１−Ｃ_４−アルキルを表し、
Ｒ^２４は、水素、それぞれ場合によりシアノ、ハロゲンまたはＣ１−Ｃ４−アルコキシで置換されたＣ_１−Ｃ_６−アルキル、Ｃ_１−Ｃ_６−アルコキシ、Ｃ_１−Ｃ_６−アルキルチオ、Ｃ_１−Ｃ_６−アルキルアミノまたはジ（Ｃ_１−Ｃ_４−アルキル）−アミノまたはそれぞれ場合によりシアノ、ハロゲンまたはＣ１−Ｃ４−アルキルで置換されたＣ_３−Ｃ_６−シクロアルキル、Ｃ_３−Ｃ_６−シクロアルキルオキシ、Ｃ_３−Ｃ_６−シクロアルキルチオまたはＣ_３−Ｃ_６−シクロアルキルアミノを表し、
Ｒ^２５は、水素、場合によりシアノ、ヒドロキシル、ハロゲンまたはＣ１−Ｃ４−アルコキシで置換されたＣ_１−Ｃ_６−アルキル、それぞれ場合によりシアノまたはハロゲンで置換されたＣ_３−Ｃ_６−アルケニルまたはＣ_３−Ｃ_６−アルキニル、または場合によりシアノ、ハロゲンまたはＣ１−Ｃ４−アルキルで置換されたＣ_３−Ｃ_６−シクロアルキルを表し、
Ｒ^２６は、水素、場合によりシアノ、ヒドロキシル、ハロゲンまたはＣ１−Ｃ４−アルコキシで置換されたＣ_１−Ｃ_６−アルキル、それぞれ場合によりシアノまたはハロゲンで置換されたＣ_３−Ｃ_６−アルケニルまたはＣ_３−Ｃ_６−アルキニル、場合によりシアノ、ハロゲンまたはＣ１−Ｃ４−アルキルで置換されたＣ_３−Ｃ_６−シクロアルキルまたは場合によりニトロ、シアノ、ハロゲン、Ｃ１−Ｃ４−アルキル、Ｃ１−Ｃ４−ハロアルキル、Ｃ１−Ｃ４−アルコキシまたはＣ１−Ｃ４−ハロアルコキシで置換されたフェニルを表し、またはＲ^２５と一緒になって、それぞれ場合によりＣ_１−Ｃ_４−アルキルで置換されたＣ_２−Ｃ_６−アルカンジイルまたはＣ_２−Ｃ_５−オキサアルカンジイルを表し、
Ｘ^４は、ニトロ、シアノ、カルボキシル、カルバモイル、ホルミル、スルファモイル、ヒドロキシル、アミノ、ハロゲン、Ｃ_１−Ｃ_４−アルキル、Ｃ_１−Ｃ_４−ハロアルキル、Ｃ_１−Ｃ_４−アルコキシまたはＣ_１−Ｃ_４−ハロアルコキシを表し、
Ｘ^５は、ニトロ、シアノ、カルボキシル、カルバモイル、ホルミル、スルファモイル、ヒドロキシル、アミノ、ハロゲン、Ｃ_１−Ｃ_４−アルキル、Ｃ_１−Ｃ_４−ハロアルキル、Ｃ_１−Ｃ_４−アルコキシまたはＣ_１−Ｃ_４−ハロアルコキシを表し、
の一般式で定義される化合物のうちの１つ、
を含む活性化合物組合せを有効量含む選択的除草組成物も提供する。

here,
t represents a numerical value of 0, 1, 2, 3, 4 or 5;
v represents a numerical value of 0, 1, 2, 3, 4 or 5;
R ²² represents hydrogen or C ₁ -C ₄ -alkyl,
R ²³ represents hydrogen or C ₁ -C ₄ -alkyl,
R ²⁴ is hydrogen, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkylthio, C ₁ -C, each optionally substituted with cyano, halogen or C1-C4-alkoxy. ₆ - alkylamino or di _(C 1 -C ₄ - alkyl) - amino or cyano optionally each halogen or C1-C4- alkyl substituted _C 3 -C ₆ - _cycloalkyl, C 3 -C ₆ - cycloalkyl _alkyloxy, C 3 -C ₆ - cycloalkylthio or _C 3 -C ₆ - cycloalkyl, amino,
R ²⁵ is C ₁ -C ₆ -alkyl substituted with hydrogen, optionally cyano, hydroxyl, halogen or C ₁ -C ₄ -alkoxy, C ₃ -C ₆ -alkenyl or C optionally substituted with cyano or halogen, respectively. ₃ -C ₆ - cycloalkyl, - alkynyl or optionally cyano, halogen or C1-C4- alkyl _C 3 substituted by -C _6,
R ²⁶ is C ₁ -C ₆ -alkyl substituted with hydrogen, optionally cyano, hydroxyl, halogen or C ₁ -C ₄ -alkoxy, C ₃ -C ₆ -alkenyl or C optionally substituted with cyano or halogen, respectively. ₃ -C ₆ - alkynyl, optionally cyano, halogen or C1-C4- alkyl _C 3 substituted by -C ₆ - cycloalkyl or optionally nitro, cyano, halogen, C1-C4- alkyl, C1-C4- haloalkyl , C1-C4- alkoxy or phenyl substituted with C1-C4- haloalkoxy, or together with ^{R 25,} _C 1 -C ₄ each optionally - _C 2 -C ₆ substituted alkyl - alkanediyl or _C 2 -C ₅ - represents oxa alkanediyl,
X ⁴ is nitro, cyano, carboxyl, carbamoyl, formyl, sulfamoyl, hydroxyl, amino, halogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy or C ₁ -C Represents ₄ -haloalkoxy,
X ⁵ is nitro, cyano, carboxyl, carbamoyl, formyl, sulfamoyl, hydroxyl, amino, halogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy or C ₁ -C Represents ₄ -haloalkoxy,
One of the compounds defined by the general formula:
There is also provided a selective herbicidal composition comprising an effective amount of an active compound combination comprising:

Formula (I) gives a general definition of the compounds according to the invention. Suitable substituents or group ranges listed in the formulas above and below are shown below.
W is preferably _hydrogen, C 1 -C ₆ - _alkyl, C 2 -C ₆ - alkenyl, _{C2-C 6} - alkynyl, _halogen, C 1 -C ₆ - _alkoxy, C 1 -C ₄ - haloalkyl, C ₁ -C ₄ - haloalkoxy or cyano,
X is preferably hydrogen, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkoxy-C ₁ -C ₄ - _alkoxy, C 1 -C ₄ - _haloalkyl, C 1 -C ₄ - haloalkoxy or cyano,
Y is preferably hydrogen, _halogen, C 1 -C ₆ - _alkyl, C 2 -C ₆ - _alkenyl, C 2 -C ₆ - _alkynyl, C 1 -C ₆ - alkoxy, _cyano, C 1 -C ₄ - Represents haloalkyl, haloalkoxy, represents V ¹ -and V ² -substituted phenyl or pyridyl,
V ¹ preferably represents halogen, C ₁ -C ₁₂ -alkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -haloalkoxy, cyano or nitro,
V ² preferably represents hydrogen, halogen, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy or C ₁ -C ₄ -haloalkyl,
V ¹ and V ² are preferably taken together, C ₃ -C ₄ -alkanediyl (optionally substituted with halogen and / or C ₁ -C ₂ -alkyl, one or two oxygen May be optionally interrupted by atoms)
Z is preferably hydrogen, _halogen, C 1 -C ₆ - haloalkoxy, - _alkyl, C 1 -C ₄ - haloalkyl, _cyano, C 1 -C ₆ - alkoxy or _C 1 -C ₄
A is preferably optionally _C 1 -C ₄ - alkyl _C 1 -C substituted with ₄ - _C 5 -C ₈ substituted with an alkyl - _C 1 -C ₄ by represents alkanediyl group, or -Cycloalkyl (optionally one methylene group is replaced by oxygen),
B preferably represents hydrogen or C ₁ -C ₈ -alkyl, C ₂ -C ₈ -alkenyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkoxy, each optionally substituted by halogen. -C ₁ -C ₄ - _alkoxy, C 1 -C ₄ - alkoxy - bis _-C 1 -C ₄ - alkoxy, optionally substituted by halogen, C1-C6- alkyl, C1-C6- alkoxy, C1-C4- haloalkyl Represents phenyl substituted by C1-C4-haloalkoxy, cyano or nitro, optionally pyridyl, pyrimidyl, thiazolyl or thienyl optionally substituted by halogen, C1-C4-alkyl or C1-C2-haloalkyl, or By halogen, C1-C4-alkyl, C1-C4-alkoxy or C1-C2-haloa C ₃ -C substituted with alkyl 8 _- two methylene groups which are not adjacent one or directly by cycloalkyl (if is replaced by oxygen, two methylene groups are substituted with a group -O-CO-, Or three methylene groups are substituted with the group -O-CO-O-).
Or A preferably represents a bond and B represents hydrogen;
D preferably represents NH or oxygen,
Q ¹ preferably represents hydrogen, or C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, each optionally substituted by halogen. C ₁ -C ₄ -alkylthio-C ₁ -C ₄ -alkyl, or C ₃ -C ₆ -cycloalkyl (optionally substituted by halogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -alkoxy) One methylene group is substituted with oxygen) or phenyl, phenyl-C ₁ -C ₂ -alkyl or hetaryl (each optionally halogen, C ₁ -C ₄ -alkyl, C ₁ -C 1- or 2-substituted with ₄ -alkoxy, C ₁ -C ₄ -haloalkyl or C ₁ -C ₄ -haloalkoxy).
Q ² preferably represents hydrogen or C ₁ -C ₆ -alkyl, or Q ¹ and Q ² together with the carbon to which they are attached, preferably a C ₃ -C ₆ -ring (optionally , Fluorine, chlorine, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy or trifluoromethyl, wherein one methylene group may optionally be replaced by oxygen. Representation or
Q ¹ and ^{Q 2,} taken together with the carbon atom to which they are attached, preferably _C 3 -C ₆ - by the ring (if, fluorine, _chlorine, C 1 -C ₄ - _alkyl, C 1 -C ₄ - 1 or 2 substituted with alkoxy or trifluoromethyl, in which one methylene group may optionally be substituted with oxygen, or
G preferably represents hydrogen (a) and represents one of the following groups:

Ｅは金属イオンまたはアンモニウムイオンを表し、
Ｌは酸素または硫黄を表し、
Ｍは酸素または硫黄を表し、
Ｒ^１は、好ましくは、それぞれ場合によりハロゲンまたはシアノで置換されたＣ_１−Ｃ_２０−アルキル、Ｃ_２−Ｃ_２０−アルケニル、Ｃ_１−Ｃ_８−アルコキシ−Ｃ_１−Ｃ_８−アルキル、Ｃ_１−Ｃ_８−アルキルチオ−Ｃ_１−Ｃ_８−アルキルまたはポリ−Ｃ_１−Ｃ_８−アルコキシ−Ｃ_１−Ｃ_８−アルキルを表し、または場合によりハロゲン、Ｃ１−Ｃ６−アルキルまたはＣ１−Ｃ６−アルコキシで置換されたＣ_３−Ｃ_８−シクロアルキル（場合により１つまたは直接隣り合わない２つのメチレン基が酸素および／または硫黄で置換される。）を表し、
好ましくは、場合によりハロゲン、シアノ、ニトロ、Ｃ１−Ｃ６−アルキル、Ｃ１−Ｃ６−アルコキシ、Ｃ１−Ｃ６−ハロアルキル、Ｃ１−Ｃ６−ハロアルコキシ、Ｃ１−Ｃ６−アルキルチオまたはＣ１−Ｃ６−アルキルスルホニルで置換されたフェニルを表し、
好ましくは、場合によりハロゲン、ニトロ、シアノ、Ｃ１−Ｃ６−アルキル、Ｃ１−Ｃ６−アルコキシ、Ｃ１−Ｃ６−ハロアルキルまたはＣ１−Ｃ６−ハロアルコキシで置換されたフェニル−Ｃ_１−Ｃ_６−アルキルを表し、
好ましくは、場合によりハロゲンまたはＣ１−Ｃ６−アルキルで置換された、酸素、硫黄、および窒素からなる群からの１個または２個のヘテロ原子を有する５員または６員ヘタリールを表し、
好ましくは、場合によりハロゲンまたはＣ１−Ｃ６−アルキルで置換されたフェノキシ−Ｃ_１−Ｃ_６−アルキルを表し、または
好ましくは、場合によりハロゲン、アミノまたはＣ１−Ｃ６−アルキルで置換された、酸素、硫黄および窒素からなる群からの１個または２個のヘテロ原子を有する５員または６員ヘタリールオキシ−Ｃ_１−Ｃ_６−アルキルを表し、
Ｒ^２は、好ましくは、それぞれ場合によりハロゲンまたはシアノで置換されたＣ_１−Ｃ_２０−アルキル、Ｃ_２−Ｃ_２０−アルケニル、Ｃ_１−Ｃ_８−アルコキシ−Ｃ_２−Ｃ_８−アルキルまたはポリ−Ｃ_１−Ｃ_８−アルコキシ−Ｃ_２−Ｃ_８−アルキルを表し、
好ましくは、場合によりハロゲン、Ｃ１−Ｃ６−アルキルまたはＣ１−Ｃ６−アルコキシで置換されたＣ_３−Ｃ_８−シクロアルキルを表し、または
好ましくは、それぞれ場合によりハロゲン、シアノ、ニトロ、Ｃ１−Ｃ６−アルキル、Ｃ１−Ｃ６−アルコキシ、Ｃ１−Ｃ６−ハロアルキルまたはＣ１−Ｃ６−ハロアルコキシで置換されたフェニルまたはベンジルを表し、
Ｒ^３は、好ましくは、場合によりハロゲンで置換されたＣ_１−Ｃ_８−アルキルまたはそれぞれ場合によりハロゲン、Ｃ１−Ｃ６−アルキル、Ｃ１−Ｃ６−アルコキシ、Ｃ１−Ｃ４−ハロアルキル、Ｃ１−Ｃ４−ハロアルコキシ、シアノまたはニトロで置換されたフェニルまたはベンジルを表し、
Ｒ^４およびＲ^５は、互いに独立して、好ましくはそれぞれ場合によりハロゲンで置換されたＣ_１−Ｃ_８−アルキル、Ｃ_１−Ｃ_８−アルコキシ、Ｃ_１−Ｃ_８−アルキルアミノ、ジ−（Ｃ_１−Ｃ_８−アルキル）アミノ、Ｃ_１−Ｃ_８−アルキルチオまたはＣ_３−Ｃ_８−アルケニルチオを表し、またはそれぞれ場合によりハロゲン、ニトロ、シアノ、Ｃ１−Ｃ４−アルコキシ、Ｃ１−Ｃ４−ハロアルコキシ、Ｃ１−Ｃ４−アルキルチオ、Ｃ１−Ｃ４−ハロアルキルチオ、Ｃ１−Ｃ４−アルキルまたはＣ１−Ｃ４−ハロアルキルで置換されたフェニル、フェノキシまたはフェニルチオを表し、
Ｒ^６およびＲ^７は、互いに独立して、好ましくは水素を表し、それぞれ場合によりハロゲンまたはシアノで置換されたＣ_１−Ｃ_８−アルキル、Ｃ_３−Ｃ_８−シクロアルキル、Ｃ_１−Ｃ_８−アルコキシ、Ｃ_３−Ｃ_８−アルケニルまたはＣ_１−Ｃ_８−アルコキシ−Ｃ_２−Ｃ_８−アルキルを表し、それぞれ場合によりハロゲン、Ｃ１−Ｃ８−アルキル、Ｃ１−Ｃ８−ハロアルキルまたはＣ１−Ｃ８−アルコキシで置換されたフェニルまたはベンジルを表し、または一緒になって、場合によりＣ_１−Ｃ_６−アルキルで置換されたＣ_３−Ｃ_６−アルキレン基（場合により１つのメチレン基が酸素または硫黄で置換される。）を表す。

E represents a metal ion or an ammonium ion;
L represents oxygen or sulfur;
M represents oxygen or sulfur,
R ¹ is preferably C ₁ -C ₂₀ -alkyl, C ₂ -C ₂₀ -alkenyl, C ₁ -C ₈ -alkoxy-C ₁ -C ₈ -alkyl, each optionally substituted by halogen or cyano, C ₁ -C ₈ - alkylthio _-C 1 -C ₈ - alkyl or poly _-C 1 -C ₈ - alkoxy _-C 1 -C ₈ - alkyl or optionally substituted by halogen,, C1-C6- alkyl or C1-C6- C ₃ -C substituted by alkoxy 8 _- cycloalkyl (. two methylene groups not adjacent one or directly optionally is substituted with oxygen and / or sulfur) it represents,
Preferably, optionally substituted with halogen, cyano, nitro, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkyl, C1-C6-haloalkoxy, C1-C6-alkylthio or C1-C6-alkylsulfonyl Represented phenyl,
Preferably, when the halogen, nitro, cyano, C1-C6- alkyl, C1-C6- alkoxy, phenyl _-C substituted with C1-C6- haloalkyl or C1-C6- haloalkoxy 1 -C ₆ - alkyl ,
Preferably, it represents a 5- or 6-membered hetaryl having 1 or 2 heteroatoms from the group consisting of oxygen, sulfur and nitrogen, optionally substituted with halogen or C1-C6-alkyl,
Preferably, it represents phenoxy-C ₁ -C ₆ -alkyl optionally substituted with halogen or C ₁ -C ₆ -alkyl, or preferably oxygen, optionally substituted with halogen, amino or C ₁ -C ₆ -alkyl, Represents 5- or 6-membered hetaryloxy-C ₁ -C ₆ -alkyl having 1 or 2 heteroatoms from the group consisting of sulfur and nitrogen;
R ² is preferably C ₁ -C ₂₀ -alkyl, C ₂ -C ₂₀ -alkenyl, C ₁ -C ₈ -alkoxy-C ₂ -C ₈ -alkyl or poly, each optionally substituted with halogen or cyano. -C ₁ -C ₈ - alkoxy _-C 2 -C ₈ - alkyl,
Preferably it represents C ₃ -C ₈ -cycloalkyl optionally substituted by halogen, C 1 -C 6 -alkyl or C 1 -C ₆ -alkoxy, or preferably each optionally halogen, cyano, nitro, C 1 -C ₆ -C 6- Represents phenyl or benzyl substituted with alkyl, C1-C6-alkoxy, C1-C6-haloalkyl or C1-C6-haloalkoxy,
R ³ is preferably C ₁ -C ₈ -alkyl optionally substituted with halogen or each optionally halogen, C1-C6-alkyl, C1-C6-alkoxy, C1-C4-haloalkyl, C1-C4-halo. Represents phenyl or benzyl substituted with alkoxy, cyano or nitro,
R ⁴ and R ⁵ are independently of each other preferably C ₁ -C ₈ -alkyl, C ₁ -C ₈ -alkoxy, C ₁ -C ₈ -alkylamino, di- (, each optionally substituted with halogen. C ₁ -C ₈ -alkyl) amino, C ₁ -C ₈ -alkylthio or C ₃ -C ₈ -alkenylthio, or each optionally halogen, nitro, cyano, C1-C4-alkoxy, C1-C4-halo Represents phenyl, phenoxy or phenylthio substituted with alkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkyl or C1-C4-haloalkyl;
R ⁶ and R ⁷ independently of one another preferably represent hydrogen, each of C ₁ -C ₈ -alkyl, C ₃ -C ₈ -cycloalkyl, C ₁ -C ₈ optionally substituted with halogen or cyano. - _alkoxy, C 3 -C ₈ - alkenyl or _C 1 -C ₈ - alkoxy _-C 2 -C ₈ - alkyl, optionally substituted by halogen, respectively, C1-C8-alkyl, C1-C8-haloalkyl or C1-C8- Represents an alkoxy substituted phenyl or benzyl, or together, a C ₃ -C ₆ -alkylene group optionally substituted with C ₁ -C ₆ -alkyl (optionally one methylene group is oxygen or sulfur); To be substituted).

  In the radical definitions described as being preferred, halogen represents fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.

W is particularly preferably hydrogen, chlorine, bromine, iodine, C ₁ -C ₄ -alkyl, C ₂ -C ₄ -alkenyl, C ₂ -C ₄ -alkynyl, C ₁ -C ₄ -alkoxy, C _1- C ₂ - haloalkyl or _C 1 -C ₂ - haloalkoxy,
X is particularly preferably chlorine, bromine, _iodine, C 1 -C ₄ - _alkyl, C 2 -C ₄ - _alkenyl, C 2 -C ₄ - _alkynyl, C 1 -C ₄ - _alkoxy, C 1 -C ₄ - alkoxy _-C 1 -C ₃ - _alkoxy, C 1 -C ₂ - _haloalkyl, C 1 -C ₂ - haloalkoxy or cyano,
Y particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methoxy, ethoxy, cyano, trifluoromethyl, difluoromethoxy or trifluoromethoxy at the 4-position;
Z particularly preferably represents hydrogen.

W also particularly preferably represents hydrogen, chlorine, bromine or C ₁ -C ₄ -alkyl,
X also particularly preferably represents chlorine, bromine, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₂ -haloalkyl, C ₁ -C ₂ -haloalkoxy or cyano,
Y also particularly preferably at _4-position, C 2 -C ₄ - _alkenyl, C 2 -C ₄ - alkynyl, group

を表し、
Ｚはまた、特に好ましくは、水素を表し、
Ｖ^１はまた、特に好ましくは、フッ素、塩素、Ｃ_１−Ｃ_４−アルキル、Ｃ_１−Ｃ_４−アルコキシ、Ｃ_１−Ｃ_２−ハロアルキルまたはＣ_１−Ｃ_２−ハロアルコキシを表し、
Ｖ^２はまた、特に好ましくは、水素、フッ素、塩素、Ｃ_１−Ｃ_４−アルキル、Ｃ_１−Ｃ_４−アルコキシまたはＣ_１−Ｃ_２−ハロアルキルを表し、
Ｖ^１およびＶ^２はまた、一緒になって、特に好ましくは、−Ｏ−ＣＨ_２−Ｏ−および−Ｏ−ＣＦ_２−Ｏ−を表す。

Represents
Z also particularly preferably represents hydrogen,
V ¹ also particularly preferably represents fluorine, chlorine, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₂ -haloalkyl or C ₁ -C ₂ -haloalkoxy,
V ² also particularly preferably represents hydrogen, fluorine, chlorine, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy or C ₁ -C ₂ -haloalkyl,
V ¹ and V ² together also particularly preferably represent —O—CH ₂ —O— and —O—CF ₂ —O—.

W likewise likewise particularly preferably represents hydrogen, chlorine, bromine or C ₁ -C ₄ -alkyl,
X likewise likewise particularly preferably represents chlorine, bromine, C ₁ -C ₄ -alkyl or C ₁ -C ₂ -haloalkyl,
Y is likewise particularly preferably at the _5-position, C 2 -C ₄ - _alkenyl, C 2 -C ₄ - alkynyl, group

を表し、
Ｚは同様に、特に好ましくは、４位で、水素、Ｃ_１−Ｃ_４−アルキルまたは塩素を表し、
Ｖ^１は同様に、特に好ましくは、フッ素、塩素、Ｃ_１−Ｃ_４−アルキル、Ｃ_１−Ｃ_４−アルコキシ、Ｃ_１−Ｃ_２−ハロアルキルまたはＣ_１−Ｃ_２−ハロアルコキシを表し、
Ｖ^２は同様に、特に好ましくは、水素、フッ素、塩素、Ｃ_１−Ｃ_４−アルキル、Ｃ_１−Ｃ_４−アルコキシまたはＣ_１−Ｃ_２−ハロアルキルを表し、
Ｖ^１およびＶ^２は同様に、一緒になって、特に好ましくは、−Ｏ−ＣＨ_２−Ｏ−または−Ｏ−ＣＦ_２−Ｏ−を表す。

Represents
Z is likewise particularly preferably in position ₄ and represents hydrogen, C ₁ -C ₄ -alkyl or chlorine,
V ¹ likewise likewise particularly preferably represents fluorine, chlorine, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₂ -haloalkyl or C ₁ -C ₂ -haloalkoxy,
V ² likewise likewise particularly preferably represents hydrogen, fluorine, chlorine, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy or C ₁ -C ₂ -haloalkyl,
V ¹ and V ² likewise together represent particularly preferably —O—CH ₂ —O— or —O—CF ₂ —O—.

W is still more particularly preferably hydrogen, C ₁ -C ₄ -alkyl, C ₂ -C ₄ -alkenyl, C ₂ -C ₄ -alkynyl, C ₁ -C ₄ -alkoxy, chlorine, bromine, iodine or tri Represents fluoromethyl,
X is still more particularly preferably chlorine, bromine, iodine, C ₁ -C ₄ -alkyl, C ₂ -C ₄ -alkenyl, C ₂ -C ₄ -alkynyl, C ₁ -C ₄ -alkoxy, C _1- C ₄ - alkoxy _-C 1 -C ₃ - _alkoxy, C 1 -C ₂ - _haloalkyl, C 1 -C ₂ - haloalkoxy or cyano,
Y is still more particularly preferably in position ₄ and represents C ₁ -C ₄ -alkyl,
Z still more preferably represents hydrogen.

W still more particularly represents hydrogen, chlorine, bromine, iodine, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -alkoxy,
X is even more, particularly preferably chlorine, bromine, _iodine, C 1 -C ₄ - _alkyl, C 1 -C ₄ - _alkoxy, C 1 -C ₂ - _haloalkyl, C 1 -C ₂ - haloalkoxy or cyano Represent,
Y is even more particularly preferably in the 4-position and represents hydrogen, chlorine, bromine, C ₁ -C ₄ -alkyl, C ₁ -C ₂ -haloalkyl or C ₁ -C ₂ -haloalkoxy,
Z is even more particularly preferably in the 3- or 5-position, fluorine, chlorine, bromine, iodine, C ₁ -C ₄ -alkyl, C ₁ -C ₂ -haloalkyl, C ₁ -C ₄ -alkoxy or C ₁ -C ₂ - represents a haloalkoxy.

A particularly preferably represents a C ₁ -C ₃ -alkanediyl group optionally substituted by C ₁ -C ₂ -alkyl, or C ₅ -C ₆ -cycloalkyl (optionally one methylene group is oxygen Is substituted.)

B is particularly preferably hydrogen or C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkoxy-C ₁ -C ₃ -alkoxy, C _1- C ₄ -alkoxy-bis-C ₁ -C ₃ -alkoxy (each optionally substituted by 1 to 3 with fluorine or chlorine) phenyl (optionally fluorine, chlorine, bromine, C ₁ -C ₄ -Alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₂ -haloalkyl, C ₁ -C ₂ -haloalkoxy, cyano or nitro substituted with 1 to 3) the stands (respectively optionally fluorine, chlorine, bromine, methyl, are 1 or 2 substituted by ethyl or trifluoromethyl.), or C ₃ -C - (. Fluorine, chlorine, methyl, are 1 or 2 substituted with methoxy or trifluoromethyl, optionally, the wherein, if two methylene groups which are not adjacent one or directly by is substituted with oxygen) cycloalkyl represents ,
Alternatively, A particularly preferably represents a bond and B represents hydrogen.

  D particularly preferably represents NH or oxygen.

Q ¹ particularly preferably represents hydrogen and represents C ₁ -C ₄ -alkyl (optionally substituted by 1 to 3 with fluorine),
Q ² particularly preferably represents hydrogen or C ₁ -C ₄ -alkyl.

Q ¹ and Q ² together with the carbon atom to which they are attached are particularly preferably monosubstituted with a C ₃ -C ₆ -ring (optionally fluorine, methyl, methoxy or trifluoromethyl, Optionally one methylene group may be substituted with oxygen), or Q ¹ and Q ² together with the carbon atoms to which they are attached are particularly preferably C ₃ -C ₆ -rings (Optionally monosubstituted with fluorine, methyl, methoxy or trifluoromethyl, wherein one methylene group may optionally be substituted with oxygen).

  G particularly preferably represents hydrogen (a) and represents one of the following groups:

式中
Ｅは金属イオンまたはアンモニウムイオンを表し、
Ｌは酸素または硫黄を表し、および
Ｍは酸素または硫黄を表す。

In the formula, E represents a metal ion or an ammonium ion,
L represents oxygen or sulfur, and M represents oxygen or sulfur.

R ¹ is particularly preferably C ₁ -C ₁₆ -alkyl, C ₂ -C ₁₆ -alkenyl, C ₁ -C ₆ -alkoxy-C ₁ -C ₄ -alkyl, C ₁ -C ₆ -alkylthio-C _1. -C ₄ - alkyl or poly _-C 1 -C ₆ - alkoxy _-C 1 _{-C 4} - (., respectively, is 1 to 3 substituted with fluorine or chlorine optionally) alkyl, or _C 3 -C ₇ - Cycloalkyl (optionally substituted by 1 to 2 with fluorine, chlorine, C ₁ -C ₅ -alkyl or C ₁ -C ₅ -alkoxy, wherein one or two non-adjacent methylene groups are optionally oxygenated and And / or substituted with sulfur)
Particularly preferred is phenyl (optionally fluorine, chlorine, bromine, cyano, nitro, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₃ -haloalkyl, C ₁ -C ₃ -haloalkoxy 1 to 3 substituted with C ₁ -C ₄ -alkylthio or C ₁ -C ₄ -alkylsulfonyl),
Particularly preferred is phenyl-C ₁ -C ₄ -alkyl (optionally fluorine, chlorine, bromine, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₃ -haloalkyl or C ₁ -C 1 to 2 substituted with ₃ -haloalkoxy).
Particular preference is given to pyrazolyl, thiazolyl, pyridyl, pyrimidinyl, furanyl or thienyl, each optionally substituted 1 to 2 with fluorine, chlorine, bromine or C ₁ -C ₄ -alkyl.
Particularly preferably, it represents phenoxy-C ₁ -C ₅ -alkyl (optionally substituted by 1 to 2 with fluorine, chlorine, bromine or C ₁ -C ₄ -alkyl), or particularly preferably pyridyloxy-C _1- C ₅ -alkyl, pyrimidyloxy-C ₁ -C ₅ -alkyl or thiazolyloxy-C ₁ -C ₅ -alkyl (in each case optionally fluorine, chlorine, bromine, amino or C ₁ -C ₄ -alkyl from 1 2).
R ² is particularly preferably C ₁ -C ₁₆ -alkyl, C ₂ -C ₁₆ -alkenyl, C ₁ -C ₆ -alkoxy-C ₂ -C ₆ -alkyl or poly-C ₁ -C ₆ -alkoxy-. Represents C ₂ -C ₆ -alkyl (each optionally substituted 1 to 3 with fluorine or chlorine) or particularly preferably C ₃ -C ₇ -cycloalkyl (optionally fluorine, chlorine, C ₁ -C ₄ -Alkyl or C ₁ -C ₄ -alkoxy substituted 1 to 2), or particularly preferably phenyl or benzyl (respectively optionally fluorine, chlorine, bromine, cyano, nitro, C ₁ -C 1 to 3 substituted with ₄ -alkyl, C ₁ -C ₃ -alkoxy, C ₁ -C ₃ -haloalkyl or C ₁ -C ₃ -haloalkoxy).
R ³ particularly preferably represents C ₁ -C ₆ -alkyl (optionally substituted by 1 to 3 with fluorine or chlorine) or phenyl or benzyl (respectively optionally fluorine, chlorine, bromine, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₂ -haloalkoxy, C ₁ -C ₂ -haloalkyl, 1 to 2 substituted with cyano or nitro).
R ⁴ and R ⁵ are, independently of one another, particularly preferably C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkylamino, di- (C ₁ -C _6- Alkyl) amino, C ₁ -C ₆ -alkylthio or C ₃ -C ₄ -alkenylthio (respectively optionally substituted by 1 to 3 with fluorine or chlorine), or phenyl, phenoxy or phenylthio (respectively optionally fluorine, chlorine, bromine, nitro, _cyano, C 1 -C ₃ - _alkoxy, C 1 -C ₃ - _haloalkoxy, C 1 -C ₃ - _alkylthio, C 1 -C ₃ - _{haloalkylthio,} C 1 -C 1 to 2 substituted with ₃ -alkyl or C ₁ -C ₃ -haloalkyl).
R ⁶ and R ⁷ independently of one another particularly preferably represent hydrogen, C ₁ -C ₆ -alkyl, C ₃ -C ₆ -cycloalkyl, C ₁ -C ₆ -alkoxy, C ₃ -C ₆ -Alkenyl or C ₁ -C ₆ -alkoxy-C ₂ -C ₆ -alkyl (respectively optionally substituted by 1 to 3 with fluorine or chlorine) phenyl or benzyl (respectively optionally fluorine, chlorine, bromine) , C ₁ -C ₅ -haloalkyl, C ₁ -C ₅ -alkyl or C ₁ -C ₅ -alkoxy 1 to 3 substituted), or together, optionally C ₁ -C ₄ -alkyl Represents a C ₃ -C ₆ -alkylene group (optionally one methylene group is substituted with oxygen or sulfur).

  In the radical definitions described as being particularly suitable, halogen represents fluorine, chlorine and bromine, in particular fluorine and chlorine.

W particularly preferably represents hydrogen, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy or trifluoromethyl;
X more particularly preferably represents chlorine, bromine, iodine, methyl, ethyl, propyl, methoxy, ethoxy, propoxy, methoxyethoxy, ethoxyethoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy or cyano,
Y is in the 4-position, more particularly preferably represents hydrogen, chlorine, bromine, iodine, trifluoromethyl or trifluoromethoxy;
Z particularly preferably represents hydrogen.

W also more particularly preferably represents hydrogen, chlorine, bromine, methyl or ethyl,
X also more particularly preferably represents chlorine, bromine, methyl, ethyl, propyl, methoxy, trifluoromethyl, difluoromethoxy or cyano,
Y also more particularly preferably represents vinyl, ethynyl, propynyl at the 4-position,

を表し、
Ｚはまた、さらに特に好ましくは、水素を表し、
Ｖ^１はまた、さらに特に好ましくは、フッ素、塩素、メチル、メトキシ、トリフルオロメチルまたはトリフルオロメトキシを表し、
Ｖ^２はまた、さらに特に好ましくは、水素、フッ素、塩素、メチル、メトキシまたはトリフルオロメチルを表す。

Represents
Z also more particularly preferably represents hydrogen,
V ¹ also more particularly preferably represents fluorine, chlorine, methyl, methoxy, trifluoromethyl or trifluoromethoxy,
V ² also more particularly preferably represents hydrogen, fluorine, chlorine, methyl, methoxy or trifluoromethyl.

W likewise likewise particularly preferably represents hydrogen, chlorine or methyl,
X likewise likewise more preferably represents chlorine, methyl or trifluoromethyl,
Y is likewise more particularly preferably in position 5 and represents vinyl, ethynyl, propynyl,

を表し、
Ｚは同様に、さらに特に好ましくは、４位で、水素またはメチルを表し、
Ｖ^１は同様に、さらに特に好ましくは、フッ素、塩素、メチル、メトキシ、トリフルオロメチルまたはトリフルオロメトキシを表し、
Ｖ^２は同様に、さらに特に好ましくは、水素、フッ素、塩素、メチル、メトキシまたはトリフルオロメチルを表す。

Represents
Z likewise likewise particularly preferably represents hydrogen or methyl at the 4-position,
V ¹ likewise likewise more preferably represents fluorine, chlorine, methyl, methoxy, trifluoromethyl or trifluoromethoxy,
V ² likewise likewise more preferably represents hydrogen, fluorine, chlorine, methyl, methoxy or trifluoromethyl.

W even more particularly preferably represents hydrogen, methyl, ethyl, methoxy, ethoxy, chlorine, bromine or iodine;
X even more particularly preferably represents chlorine, bromine, iodine, methyl, ethyl, propyl, methoxy, ethoxy, propoxy, methoxyethoxy, ethoxyethoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy or cyano,
Y is even more particularly preferably in position 4 and represents methyl or ethyl,
Z even more particularly preferably represents hydrogen.

W even more particularly preferably represents hydrogen, chlorine, bromine, iodine, methyl or ethyl;
X even more particularly preferably represents chlorine, bromine, iodine, methyl, ethyl, methoxy, trifluoromethyl, difluoromethoxy or trifluoromethoxy,
Y is even more particularly preferably in position 4 and represents hydrogen, chlorine, bromine, iodine, methyl or ethyl;
Z is even more particularly preferably in the 3 or 5 position, fluorine, chlorine, bromine, iodine, methyl, ethyl, trifluoromethyl or trifluoromethoxy.

A is very particularly _{preferably, -CH 2 -, - CHCH 3} -, - CH 2 -CH 2 -, - CH 2 -CHCH 3 -, - represents a - CH ₂ -CH ₂ -CH _2.

B particularly preferably represents hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, C ₂ -C ₄ -alkenyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, methoxyethoxy, ethoxyethoxy. , Phenyl (optionally fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro substituted 1 or 2), cyclopropyl, cyclopentyl or cyclohexyl (optionally 1 Two methylene groups are substituted with oxygen).
Alternatively, A particularly preferably represents a bond and B represents hydrogen.

  D particularly preferably represents NH or oxygen.

Q ¹ more particularly preferably represents hydrogen, methyl or ethyl.

Q ² more particularly preferably represents hydrogen, methyl or ethyl.

Q ¹ and Q ² together with the carbon atom to which they are attached more particularly preferably represent cyclopropyl, cyclopentyl, or cyclohexyl, or Q ¹ and Q ² together with the carbon atom to which they are attached And more particularly preferably represents a C ₅ -C ₆ -ring (optionally interrupted by oxygen).

  G represents hydrogen (a), and represents one of the following groups:

Ｅは金属イオンまたはアンモニウムイオンを表し、
Ｌは酸素または硫黄を表し、および
Ｍは酸素または硫黄を表す。

E represents a metal ion or an ammonium ion;
L represents oxygen or sulfur, and M represents oxygen or sulfur.

R ¹ is more particularly preferably C ₁ -C ₁₀ -alkyl, C ₂ -C ₁₀ -alkenyl, C ₁ -C ₄ -alkoxy-C ₁ -C ₂ -alkyl, C ₁ -C ₄ -alkylthio-C. ₁ -C ₂ -alkyl (each optionally substituted by 1 to 3 with fluorine or chlorine) or C ₃ -C ₆ -cycloalkyl (optionally substituted with fluorine, chlorine, methyl, ethyl or methoxy) Represents)
More particularly preferably, phenyl (optionally substituted by 1 to 2 with fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, trifluoromethyl or trifluoromethoxy). Represent,
More particularly preferably, it represents furanyl, thienyl or pyridyl (in each case optionally substituted with chlorine, bromine or methyl).
R ² more particularly preferably represents C ₁ -C ₁₀ -alkyl, C ₂ -C ₁₀ -alkenyl or C ₁ -C ₄ -alkoxy-C ₂ -C ₄ -alkyl (in each case optionally with fluorine or chlorine). 1 to 3 substituted.) Or more particularly preferably represents cyclopentyl or cyclohexyl,
Or more particularly preferably represents phenyl or benzyl, each optionally substituted 1 to 2 with fluorine, chlorine, cyano, nitro, methyl, ethyl, methoxy, trifluoromethyl or trifluoromethoxy.
R ³ more particularly preferably represents methyl, ethyl, propyl or isopropyl (respectively optionally substituted by 1 to 3 with fluorine or chlorine) or phenyl (optionally fluorine, chlorine, bromine, methyl, ethyl, Isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro.
R ⁴ and R ⁵ , independently of one another, more particularly preferably represent C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -alkylthio, or represent phenyl, phenoxy or phenylthio (in each case optionally fluorine, Monosubstituted with chlorine, bromine, nitro, cyano, methyl, methoxy, trifluoromethyl or trifluoromethoxy).
R ⁶ and R ⁷ independently of one another more particularly preferably represent hydrogen, C ₁ -C ₄ -alkyl, C ₃ -C ₆ -cycloalkyl, C ₁ -C ₄ -alkoxy, C ₃ -C Represents ₄ -alkenyl or C ₁ -C ₄ -alkoxy-C ₂ -C ₄ -alkyl and represents phenyl (optionally substituted 1 to 2 with fluorine, chlorine, bromine, methyl, methoxy or trifluoromethyl). Or together represent a C ₅ -C ₆ -alkylene group (optionally one methylene group is replaced by oxygen or sulfur).

W particularly preferably represents methyl, ethyl or methoxy,
X particularly preferably represents chlorine, methyl, ethyl or methoxy,
Y is particularly preferably in position 4 and represents chlorine or bromine;
Z particularly preferably represents hydrogen.

W likewise likewise preferably represents hydrogen,
X likewise likewise preferably represents methyl,
Y is likewise particularly preferably in the 5-position,

を表し、
Ｚは、特別に好ましくは、４位で、水素を表す。

Represents
Z is particularly preferably in position 4 and represents hydrogen.

W still more particularly preferably represents methyl or ethyl;
X still more particularly preferably represents chlorine, bromine or methyl;
Y is even more particularly preferably in position 4 and represents methyl;
Z even more particularly preferably represents hydrogen.

A particularly preferably represents —CH ₂ — or —CH ₂ —CH ₂ —,
B particularly preferably represents hydrogen, methyl, ethyl, propyl, methoxy or cyclopropyl,
Alternatively, A particularly preferably represents a bond and B represents hydrogen.

  D particularly preferably represents NH.

Q ¹ particularly preferably represents hydrogen.

Q ² particularly preferably represents hydrogen.

  G particularly preferably represents hydrogen (a) and represents one of the following groups:

最も好ましくは水素、（ｂ）基、および（ｃ）基であり、
式中
Ｅは金属イオンを表し、
Ｌは酸素を表し、および
Ｍは酸素を表す。

Most preferred are hydrogen, (b) group, and (c) group,
Where E represents a metal ion,
L represents oxygen, and M represents oxygen.

R ¹ particularly preferably represents C ₁ -C ₁₀ -alkyl,
Represents phenyl (optionally 1 substituted with chlorine);
R ² particularly preferably represents C ₁ -C ₁₀ -alkyl or C ₂ -C ₁₀ -alkenyl,
R ³ particularly preferably represents methyl;
R ⁶ and R ⁷ together represent a C ₅ -C ₆ -alkylene group (optionally one methylene group is replaced with oxygen).

  The general or preferred group definitions or illustrations listed above can be combined with one another as desired. That is, the combination between each range and a preferable range is included. These also apply to the final product and the corresponding precursors and intermediates.

  Preferred according to the invention are compounds of the formula (I) which contain a combination of the meanings listed above as being suitable.

  Particularly preferred according to the invention are compounds of the formula (I) which contain combinations of the meanings listed above as being particularly suitable.

  Even more particularly preferred according to the invention are compounds of the formula (I) comprising combinations of the meanings listed above as being even more particularly preferred.

  Particularly preferred according to the invention are compounds of the formula (I) which contain combinations of the meanings listed above as being particularly suitable.

  Saturated or unsaturated hydrocarbon groups (such as alkyl, alkanediyl or alkenyl) may be linear or branched wherever possible, including in combination with heteroatoms (eg, in alkoxy, etc.) Can be.

  Unless otherwise indicated, optionally substituted groups may be mono- or polysubstituted, and in the case of polysubstitution, the substituents may be the same or different.

  In addition to the compounds described in the Preparation Examples, the following compounds of formula (I-1-a) can be specifically described.

表２：Ａ、Ｗ、Ｘ、ＹおよびＺは、表１に記載のとおり
Ｂ＝ＣＨ_３
表３：Ａ、Ｗ、Ｘ、ＹおよびＺは、表１に記載のとおり
Ｂ＝Ｃ_２Ｈ_５
表４：Ａ、Ｗ、Ｘ、ＹおよびＺは、表１に記載のとおり
Ｂ＝Ｃ_３Ｈ_７
表５：Ａ、Ｗ、Ｘ、ＹおよびＺは、表１に記載のとおり
Ｂ＝ｉ−Ｃ_３Ｈ_７
表６：Ａ、Ｗ、Ｘ、ＹおよびＺは、表１に記載のとおり

Table 2: A, W, X, Y and Z are as described in Table 1 B = CH ₃
Table 3: A, W, X, Y and Z are as described in Table 1 B = C ₂ H ₅
Table 4: A, W, X, Y and Z are as described in Table 1 B = C ₃ H ₇
Table 5: A, W, X, Y and Z are as described in Table 1 B = i-C ₃ H ₇
Table 6: A, W, X, Y and Z are as described in Table 1.

表７：Ａ、Ｗ、Ｘ、ＹおよびＺは、表１に記載のとおり

Table 7: A, W, X, Y and Z are as described in Table 1.

表８：Ａ、Ｗ、Ｘ、ＹおよびＺは表１に記載のとおり
Ａ＝−ＣＨ_２−ＣＨ_２−；Ｂ＝ＯＣＨ_３
表９：Ａ、Ｗ、Ｘ、ＹおよびＺは表１に記載のとおり
Ａ＝−ＣＨ_２−ＣＨ_２−；Ｂ＝ＯＣ_２Ｈ_５

Table 8: A, W, X, Y and Z are as described in Table 1 A = —CH ₂ —CH ₂ —; B = OCH ₃
Table 9: A, W, X, Y and Z are as described in Table 1 A = —CH ₂ —CH ₂ —; B = OC ₂ H ₅

  In addition to the compounds described in the Preparation Examples, the following compounds of formula (I-2-a) can be specifically described.

表１１：Ａ、Ｗ、Ｘ、ＹおよびＺは、表１０に記載のとおり
Ｂ＝ＣＨ_３
表１２：Ａ、Ｗ、Ｘ、ＹおよびＺは、表１０に記載のとおり
Ｂ＝Ｃ_２Ｈ_５
表１３：Ａ、Ｗ、Ｘ、ＹおよびＺは、表１０に記載のとおり
Ｂ＝Ｃ_３Ｈ_７
表１４：Ａ、Ｗ、Ｘ、ＹおよびＺは、表１０に記載のとおり
Ｂ＝ｉ−Ｃ_３Ｈ_７
表１５：Ａ、Ｗ、Ｘ、ＹおよびＺは、表１０に記載のとおり

Table 11: A, W, X, Y and Z are as described in Table 10 B = CH ₃
Table 12: A, W, X, Y and Z are as described in Table 10 B = C ₂ H ₅
Table 13: A, W, X, Y and Z are as described in Table 10 B = C ₃ H ₇
Table 14: A, W, X, Y and Z are as described in Table _{10 B = i-C 3 H} 7
Table 15: A, W, X, Y and Z are as described in Table 10

表１６：Ａ、Ｗ、Ｘ、ＹおよびＺは、表１０に記載のとおり

Table 16: A, W, X, Y and Z are as described in Table 10

表１７：Ｗ、Ｘ、ＹおよびＺは、表１０に記載のとおり
Ａ＝−ＣＨ_２−ＣＨ_２−；Ｂ＝ＯＣＨ_３
表１８：Ｗ、Ｘ、ＹおよびＺは、表１０に記載のとおり
Ａ＝−ＣＨ_２−ＣＨ_２−；Ｂ＝ＯＣ_２Ｈ_５

Table 17: W, X, Y and Z are as described in Table 10 A = —CH ₂ —CH ₂ —; B═OCH ₃
Table 18: W, X, Y and Z are as described in Table 10 A = —CH ₂ —CH ₂ —; B = OC ₂ H ₅

  Preferred definitions of the groups listed above in relation to crop compatibility improving compounds of formulas (IIa), (IIb), (IIc), (IId), and (IIe) (“herbicide safeners”) Is defined below.

  m preferably represents a numerical value of 0, 1, 2, 3 or 4.

A ¹ preferably represents one of the divalent heterocyclic groups shown below

ｎは、好ましくは、０、１、２、３または４の数値を表す。

n preferably represents a numerical value of 0, 1, 2, 3 or 4.

A ² preferably represents methylene or ethylene, each optionally substituted with methyl, ethyl, methoxycarbonyl, ethoxycarbonyl or allyloxycarbonyl.

R ¹⁴ is preferably hydroxyl, mercapto, amino, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, It represents i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino.

R ¹⁵ is preferably hydroxyl, mercapto, amino, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, 1-methylhexyloxy, allyloxy, 1-allyloxymethylethoxy , Methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t- Represents butylamino, dimethylamino or diethylamino.

R ¹⁶ preferably represents methyl, ethyl, n- or i-propyl, each optionally substituted with fluorine, chlorine and / or bromine.

R ¹⁷ is preferably hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl, butenyl, each optionally substituted with fluorine and / or chlorine. Propynyl or butynyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, dioxolanylmethyl, furyl, furylmethyl, thienyl, thiazolyl, piperidinyl, or optionally fluorine-, chlorine-, methyl-, ethyl-, n- or Represents i-propyl-, n-, i-, s- or t-butyl-substituted phenyl.

R ¹⁸ is preferably hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl, butenyl, propynyl, each optionally substituted with fluorine and / or chlorine. Or butynyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, dioxolanylmethyl, furyl, furylmethyl, thienyl, thiazolyl, piperidinyl, or optionally fluorine, chlorine, methyl, ethyl, n- or i-propyl, n -, i-, represents phenyl substituted by s- or t- butyl, or together with _{^{R 17, -CH 2 -O-CH}} 2 -CH 2 - and _-CH 2 _-CH 2 -O- Represents one of the groups CH ₂ —CH ₂ — (optionally methyl, ethyl, furyl, phenyl, Substituted with a benzene ring and substituted with two substituents, which together with the C atoms to which they are attached form a 5- or 6-membered carbocycle).

R ¹⁹ preferably represents hydrogen, cyano, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, cyclopropyl, cyclobutyl, each optionally substituted with fluorine, chlorine and / or bromine, Represents cyclopentyl, cyclohexyl or phenyl.

R ²⁰ is preferably hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, each optionally substituted by hydroxyl, cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy. , S- or t-butyl.

R ²¹ preferably represents hydrogen, cyano, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, n-, i-, each optionally substituted with fluorine, chlorine and / or bromine. , S- or t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl.

X ¹ is preferably nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl. , Trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy.

X ² is preferably hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, tri Represents fluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy.

X ³ is preferably hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trimethyl. Represents fluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy.

  t preferably represents a numerical value of 0, 1, 2, 3 or 4.

  v preferably represents a numerical value of 0, 1, 2, 3 or 4.

R ²² preferably represents hydrogen, methyl, ethyl, n- or i-propyl.

R ²³ preferably represents hydrogen, methyl, ethyl, n- or i-propyl.

R ²⁴ is preferably hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s, each optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy. -Or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino or optionally cyano, fluorine, chlorine, bromine, methyl, Cyclopropyl, cyclobutyl, cyclopentyl substituted with ethyl n- or i-propyl , Cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino or cyclohexylamino.

R ²⁵ is preferably hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, each optionally substituted with cyano, hydroxyl, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy. Or s-butyl, each optionally substituted with cyano, fluorine, chlorine, or bromine, propenyl, butenyl, propynyl, or butynyl, or each optionally cyano, fluorine, chlorine, bromine, methyl, ethyl n- or i-propyl Represents cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl substituted with

R ²⁶ is preferably hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, each optionally substituted with cyano, hydroxyl, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy. Or s-butyl, each optionally with propenyl, butenyl, propynyl, or butynyl substituted with cyano, fluorine, chlorine, or bromine, optionally with cyano, fluorine, chlorine, bromine, methyl, ethyl n- or i-propyl, respectively Substituted cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl, or optionally nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, Trifluoromethyl, methoxy, ethoxy, n-if Represents phenyl substituted by i-propoxy, difluoromethoxy or trifluoromethoxy, or butane-1,4-diyl (trimethylene), together with R ²⁵ , optionally substituted with methyl or ethyl, It represents pentane-1,5-diyl, 1-oxabutane-1,4-diyl, or 3-oxapentane-1,5-diyl.

X ⁴ is preferably nitro, cyano, carboxyl, carbamoyl, formyl, sulfamoyl, hydroxyl, amino, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t -Represents butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy.

X ⁵ is preferably nitro, cyano, carboxyl, carbamoyl, formyl, sulfamoyl, hydroxyl, amino, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t -Represents butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy.

  Examples of compounds of formula (IIa) that are particularly particularly suitable as herbicide safeners according to the invention are listed in Table 19 below.

Table 19: Examples of compounds of formula (IIa)

  Examples of compounds of formula (IIb) that are particularly particularly suitable as herbicide safeners according to the invention are listed in Table 20 below.

表２０：式（ＩＩｂ）の化合物の例

Table 20: Examples of compounds of formula (IIb)

  Examples of compounds of the formula (IIc) that are particularly particularly suitable as herbicide safeners according to the invention are listed in Table 21 below.

表２１：式（ＩＩｃ）の化合物の例

Table 21: Examples of compounds of formula (IIc)

  Examples of compounds of the formula (IId) that are particularly particularly suitable as herbicide safeners according to the invention are listed in Table 22 below.

表２２：式（ＩＩｄ）の化合物の例

Table 22: Examples of compounds of formula (IId)

  Examples of compounds of formula (IIe) that are particularly particularly suitable as herbicide toxicity mitigators according to the invention are listed in Table 23 below.

表２３：式（ＩＩｅ）の化合物の例

Table 23: Examples of compounds of formula (IIe)

  Most suitable as the crop compatibility improving compound [component (b ′)] is cloquintoset mexil, fenchlorazole ethyl, oxadiphenethyl, mefenpyrdiethyl, flirazole, fenchlorim, cumyluron, diimron, dimepiperate, And compound IIe-5 (cyprosulfamide) and compound IIe-11, and of particular importance are croquintoset mexyl and mefenpyrdiethyl, as well as oxadiphenethyl and ( sand) Cyprosulfamide.

  The compounds of the general formula (IIa) to be used as safeners according to the invention are known and / or can be prepared by processes known per se (Note: WO-A-91 / 07874, WO -A-95 / 07897).

  The compounds of the general formula (IIb) to be used as safeners according to the invention are known and / or can be prepared by processes known per se (Note, EP-A-191736).

  The compounds of the general formula (IIc) to be used as safeners according to the invention are known and / or can be prepared by processes known per se (note, DE-A-2218097, DE-A -2350547).

  The compounds of the general formula (IId) to be used as safeners according to the invention are known and / or can be prepared by processes known per se (Note, DE-A-19621522 / US-A) -62335680).

  The compounds of the general formula (IIe) to be used as safeners according to the invention are known and / or can be prepared by processes known per se (Note, WO-A-99 / 66795 / US -A-6251827).

  Examples of selective herbicidal combinations according to the invention, each comprising one active compound of the formula (I) and one of the safeners, as defined above, are listed in Table 24 below.

  Surprisingly, the active compound combinations as defined above of substituted cyclic ketoenols of the general formula (I) and safeners (antidotes) from the group (b ′) above are useful for useful plants. Is well-tolerated, but has a particularly high herbicidal activity, so it is used in various crops, especially cereals (especially wheat), as well as soybeans, potatoes, corn and rice for the selective control of weeds It was found here that we can do it.

  Of the many known safeners or antidotes that can antagonize the harmful effects of herbicides on crops, suitable are the compounds of group (b ′) above, especially these It is surprising that there is virtually no such detrimental effect on the herbicidal activity against weeds, eliminating the detrimental effects of substituted cyclic ketoenols on crops.

  Particularly preferred and most preferred combination partners from group (b '), especially for cereal plants such as wheat, barley and rye as well as corn and rice as crop plants. The particularly advantageous effects of can be emphasized.

  In the literature it has already been described how the action of various active compounds can be enhanced by the addition of ammonium salts. However, the salt is a salt having a detergency effect (eg WO 95/017817) and has a relatively long alkyl and / or aryl substituent to have a permeation effect or increase the solubility of the active compound (E.g. EP-A0453086, EP-A0664081, FR-A26000494, US4844734, US54662912, US5533937, US-A03 / 0224939, US-A05 / 0009880, US-A05 / 0096386). Moreover, the prior art describes the action of specific active compounds and / or corresponding compositions only on specific applications. Next, in this other case, the salt is a salt of sulfonic acid, and the acid itself has an anesthetic action on insects (US2842476). Enhancement of the action by ammonium sulfate is described, for example, for the herbicide glyphosate, or phosphinotricin (US 6645914, EP-A20036106). The corresponding action in the case of insecticides has not been described or suggested by this prior art.

  The use of ammonium sulfate as a formulation aid has also been described for certain active compounds and applications (WO 92/16108), but the aim here is not to enhance the action but to stabilize the formulation.

  Quite surprisingly, the action of pesticides and / or acaricides and / or herbicides from the class of 3′-alkoxyspirocyclopentyl-substituted tetramic acids and tetronic acids is the effect of ammonium or phosphonium salts on the application solution. It has now been found that it can be significantly enhanced through addition or through incorporation of these salts into formulations containing 3′-alkoxyspirocyclopentyl substitutions. Accordingly, the present invention enhances the action of crop protection compositions comprising insecticidal and / or acaricidal 3′-alkoxyspirocyclopentyl substituted tetramic acid and tetronic acid as the active compounds tetrametic acid and tetronic acid of the composition Use of an ammonium salt or phosphonium salt to provide Similarly, the present invention provides a composition comprising an insecticidal 3′-alkoxyspirocyclopentyl-substituted tetramic acid and tetronic acid and an action-enhancing ammonium or phosphonium salt, which is ready to use as well as active compound formulations. Contains composition (spray solution). Finally, the present invention further provides the use of such compositions for controlling pests and / or spider mites and / or undesirable vegetation. Such a composition may also include a crop suitability improving compound as described above.

  The active compounds can be used in the compositions according to the invention in a wide concentration range. The concentration of the active compound in the formulation is typically 0.1% to 50% by weight.

  Ammonium and phosphonium salts that enhance the activity of crop protection compositions comprising fatty acid biosynthesis inhibitors according to the present invention are represented by the following formula (III '):

式中、
Ｄは窒素またはリンを表し、
Ｄは好ましくは窒素を表し、
Ｒ^２６、Ｒ^２７、Ｒ^２８およびＲ^２９は、互いに独立して、水素またはそれぞれ場合により置換されたＣ_１−Ｃ_８−アルキルまたは一不飽和もしくは多不飽和の、場合により置換されたＣ_１−Ｃ_８−アルキレンを表し、置換基はハロゲン、ニトロ、およびシアノから選択され、
Ｒ^２６、Ｒ^２７、Ｒ^２８およびＲ^２９は、互いに独立して、好ましくは、水素またはそれぞれ場合により置換されたＣ_１−Ｃ_４−アルキルを表し、置換基はハロゲン、ニトロ、およびシアノから選択され、
Ｒ^２６、Ｒ^２７、Ｒ^２８およびＲ^２９は、互いに独立して、特に好ましくは、水素、メチル、エチル、ｎ−プロピル、イソプロピル、ｎ−ブチル、イソブチル、ｓｅｃ−ブチルまたはｔｅｒｔ−ブチルを表し、
Ｒ^２６、Ｒ^２７、Ｒ^２８、およびＲ^２９は、さらに特に好ましくは、水素を表し、
ｎは、１、２、３または４を表し、
ｎは、好ましくは１または２を表し、
Ｒ^３０は、有機アニオンまたは無機アニオンを表し、
Ｒ^３０は、好ましくは、炭酸水素塩、四ホウ酸塩、フッ化物、臭化物、ヨウ化物、塩化物、リン酸一水素塩、リン酸二水素塩、硫酸水素塩、酒石酸塩、硫酸塩、硝酸塩、チオ硫酸塩、チオシアン酸塩、ギ酸塩、乳酸塩、酢酸塩、プロピオン酸塩、酪酸塩、ペンタン酸塩、またはシュウ酸塩を表し、
Ｒ^３０は、特に好ましくは、乳酸塩、硫酸塩、硝酸塩、チオ硫酸塩、チオシアン酸塩、シュウ酸塩、またはギ酸塩を表し
Ｒ^３０は、さらに特に好ましくは、硫酸塩を表し、
で定義される。

Where
D represents nitrogen or phosphorus;
D preferably represents nitrogen,
R ²⁶ , R ²⁷ , R ²⁸ and R ²⁹ are, independently of one another, hydrogen or each optionally substituted C ₁ -C ₈ -alkyl or monounsaturated or polyunsaturated optionally substituted C ₁ -C 8 _- alkylene, the substituents are selected from halogen, nitro, and cyano,
R ²⁶ , R ²⁷ , R ²⁸ and R ²⁹ independently of one another preferably represent hydrogen or each optionally substituted C ₁ -C ₄ -alkyl, the substituents being selected from halogen, nitro and cyano And
R ²⁶ , R ²⁷ , R ²⁸ and R ²⁹ independently of one another particularly preferably represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl,
R ²⁶ , R ²⁷ , R ²⁸ and R ²⁹ more particularly preferably represent hydrogen,
n represents 1, 2, 3 or 4;
n preferably represents 1 or 2,
R ³⁰ represents an organic or inorganic anion,
R ³⁰ is preferably bicarbonate, tetraborate, fluoride, bromide, iodide, chloride, monohydrogen phosphate, dihydrogen phosphate, hydrogen sulfate, tartrate, sulfate, nitrate , Thiosulfate, thiocyanate, formate, lactate, acetate, propionate, butyrate, pentanoate, or oxalate,
R ³⁰ particularly preferably represents lactate, sulfate, nitrate, thiosulfate, thiocyanate, oxalate or formate, and R ³⁰ even more particularly preferably represents sulfate,
Defined by

  The ammonium and phosphonium salts of formula (III ') can be used in a wide concentration range to enhance the activity of crop protection compositions containing ketoenols. In general, ammonium or phosphonium salts are used in ready-to-use crop protection compositions at concentrations of 0.5 to 80 mmol / l, preferably 0.75 to 37.5 mmol / l, more preferably 1.5 to 25 mmol / l. Used in In the case of formulated products, the ammonium salt and / or phosphonium salt concentration in the formulation is within the general, preferred, or particularly preferred range after the formulation is diluted so that the active ingredient is at the desired concentration. Selected to be within the stated range. The salt concentration in the formulation is typically 1% to 50% by weight.

  In one preferred embodiment of the invention, the activity is enhanced by adding not only ammonium and / or phosphonium salts but also penetrants to the crop protection composition. Even so, it is quite surprising that a greater enhancement to activity is observed. Thus, similarly, the present invention provides penetrants and ammonium salts and / or to enhance the activity of crop protection compositions comprising 3'-alkoxyspirocyclopentyl substituted tetramic acid and tetronic acid having insecticidal properties as active compounds. Use of a combination with a phosphonium salt is provided. Similarly, the present invention provides a composition comprising a 3′-alkoxyspirocyclopentyl substituted tetramic acid and tetronic acid having herbicidal and / or acaricidal and / or insecticidal properties, penetrants and ammonium and / or phosphonium salts. Provided, specifically including not only the formulated active compound but also ready-to-use compositions (spray solutions). Finally, the present invention further provides the use of such compositions for controlling pests.

  Suitable penetrants in the present invention include all such substances commonly used to improve the penetration of active agrochemical compounds into plants. Penetration agents are defined in the present invention for their ability to penetrate the plant cuticle from the aqueous spray and / or from the spray coating, thereby increasing the mobility of the active compound in the cuticle. In order to determine this property, methods described in the literature (Baur et al., 1997, Pesticide Science 51, 131-152) can be used.

An example of a suitable penetrant is alkanol alkoxylate. The penetrant of the present invention is an alkanol alkoxylate of the following formula (IV ′):
R—O — (— AO) _v —R ′ (IV ′)
Where
R represents straight-chain or branched alkyl having 4 to 20 carbon atoms,
R ′ represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl or n-hexyl;
AO represents ethylene oxide group, propylene oxide group, butylene oxide group, and is a mixture of ethylene oxide and propylene oxide group or butylene oxide group;
v represents a numerical value of 2 to 30.

One suitable group of penetrants are alkanol alkoxylates of the formula: R—O — (— EO—) _n —R ′ (IV′-a)
Where
R is as defined above;
R ′ is as defined above;
EO represents —CH ₂ —CH ₂ —O—,
n represents a numerical value of 2 to 20

An even more preferred group of penetrants are alkanol alkoxylates of the formula
R—O — (— EO—) _p — (— PO—) _q —R ′ (IV′-b)
Where
R is as defined above;
R ′ is as defined above;
EO represents —CH ₂ —CH ₂ —O—,
PO is

を表し、
ｐは、１から１０の数値を表し、
ｑは、１から１０の数値を表す。

Represents
p represents a number from 1 to 10,
q represents a numerical value of 1 to 10.

An even more preferred group of penetrants are alkanol alkoxylates of the formula
R—O — (— PO—) _r — (EO—) _s —R ′ (IV′-c)
Where
R is as defined above;
R ′ is as defined above;
EO is _-CH 2 _-CH 2 -O- and represent,
PO is

を表し、
ｒは、１から１０の数値を表し、
ｓは、１から１０の数値を表す。

Represents
r represents a numerical value from 1 to 10,
s represents a numerical value from 1 to 10.

Even more preferred groups of penetrants are alkanol alkoxylates of the formula
R—O — (— EO—) _p — (— BO—) _q —R ′ (IV′-d)
Where
R and R ′ are as defined above;
EO is _CH 2 _-CH 2 -O- and represent,
BO is

を表し、
ｐは、１から１０の数値を表し、
ｑは、１から１０の数値を表す。

Represents
p represents a number from 1 to 10,
q represents a numerical value of 1 to 10.

Even more preferred groups of penetrants are the following formulas R—O — (— BO—) _r — (— EO—) _s —R ′ (IV′-e)
Where
R and R ′ are as defined above;
BO is

を表し、
ＥＯはＣＨ_２−ＣＨ_２−Ｏ−を表し、
ｒは、１から１０の数値を表し、
ｓは、１から１０の数値を表し、
のアルカノールアルコキシレートである。

Represents
EO is _CH 2 _-CH 2 -O- and represent,
r represents a numerical value from 1 to 10,
s represents a numerical value from 1 to 10,
The alkanol alkoxylate.

Even more preferred groups of penetrants are alkanol alkoxylates of the formula
_{CH 3 - (CH 2) t} -CH 2 -O - (- CH 2 -CH 2 -O-) u-R '(IV'-f)
Where
R ′ is as defined above;
t represents a number from 8 to 13,
u represents a numerical value of 6 to 17.

In the formula shown above,
R is preferably butyl, isobutyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-octyl, isooctyl, 2-ethylhexyl, nonyl, ionoyl, decyl, n-dodecyl, isododecyl, lauryl, myristyl , Isotridecyl, trimethylnonyl, palmityl, stearyl, or eicosyl.

  Examples of alkanol alkoxylates of formula (IV'-c) include 2-ethylhexyl alkoxylates of the following formula:

式中、
ＥＯは−ＣＨ_２−ＣＨ_２−Ｏ−を表し、
ＰＯは、

Where
EO is _-CH 2 _-CH 2 -O- and represent,
PO is

を表し、
８および６の数値は、平均値を表す。

Represents
Numerical values 8 and 6 represent average values.

Examples of alkanol alkoxylates of formula (IV′-d) include the following formulas CH ₃ — (CH ₂ ) ₁₀ —O — (— EO—) ₆ — (— BO—) ₂ —CH ₃ (IV′-d -1)
Where
EO is _CH 2 _-CH 2 -O- and represent,
BO is

を表し、
１０、６および２の数値は、平均値を表す
を挙げることができる。

Represents
The numerical values of 10, 6 and 2 can represent average values.

Particularly preferred alkanol alkoxylates of the formula (IV′-f) are compounds of this formula,
t represents a numerical value from 9 to 12,
u represents a numerical value of 7 to 9.

More particularly, the formula (IV′-f-1)
_{CH 3 - (CH 2) t} -CH 2 -O - (- CH 2 -CH 2 -O-) u -H (IV'-f-1)
Where
t represents an average value of 10.5;
u represents an average value of 8.4,
The alkanol alkoxylate can be mentioned.

  A general definition of an alkanol alkoxylate is given by the above formula. These substances are mixtures of the described types of compounds with different chain lengths. Thus, the index has an average value and may deviate from an integer.

  The alkanol alkoxylates of the formula described are known and can be prepared by known methods, possibly commercially available (Note, WO 98/35553, WO 00/35278, and EP-A 068 865).

  Suitable penetrants also include, for example, substances that facilitate the availability of compounds of formula (I) in spray coatings. Such includes, for example, mineral oils or vegetable oils. Suitable oils are all mineral oils or vegetable oils, modified or unmodified, that can usually be used in agrochemical compositions. Examples include sunflower oil, rapeseed oil, olive oil, castor oil, rapeseed oil, corn seed oil, cottonseed oil, and soybean oil, or esters of such oils. Rapeseed oil, sunflower oil, and methyl or methyl esters thereof are preferred.

  The concentration of penetrant in the composition of the present invention can vary over a wide range. In the case of formulated crop protection compositions, the concentration is generally from 1% to 95% by weight, preferably from 1% to 55% by weight, more preferably from 15% to 40% by weight. For ready-to-use compositions (spray solutions), the concentration is generally between 0.1 and 10 g / l, preferably between 0.5 and 5 g / l.

  The crop protection composition of the present invention may also include additional components, examples include surfactants and / or dispersion aids or emulsifiers.

  Suitable nonionic surfactants and / or dispersion aids include all such materials that can be commonly used in agrochemical compositions. Preferably, a polyethylene oxide-polypropylene oxide block copolymer, a polyethylene glycol ether of a linear alcohol, a reaction product of a fatty acid with ethylene oxide and / or propylene oxide, and a copolymer of polyvinyl alcohol, polyvinyl pyrrolidone, polyvinyl alcohol and polyvinyl pyrrolidone. Mention may be made of polymers and copolymers of (meth) acrylic acid and (meth) acrylic esters, as well as alkyl ethoxylates and alkylaryl ethoxylates, which may optionally be phosphorylated and May be neutralized with a base, and examples include sorbitol ethoxylates and polyoxyalkyleneamine derivatives.

  Suitable anionic surfactants include all such materials that can be commonly used in agrochemical compositions. Alkali metal salts and alkaline earth metal salts of alkylsulfonic acid or alkylarylsulfonic acid are preferred.

  A further more preferred group of anionic surfactants and / or dispersion aids are the following salts with low solubility in vegetable oils. A salt of polystyrene sulfonic acid, a salt of polyvinyl sulfonic acid, a salt of naphthalene sulfonic acid-formaldehyde condensate, a salt of a condensation product of naphthalene sulfonic acid, phenol sulfonic acid and formaldehyde, and a salt of lignosulfonic acid.

  Suitable additives that may be included in the formulations of the present invention are emulsifiers, anti-foaming agents, preservatives, antioxidants, colorants, and inert filler materials.

  Suitable emulsifiers are ethoxylated nonylphenol, reaction products of alkylphenols with ethylene oxide and / or propylene oxide, ethoxylated arylalkylphenols, and ethoxylated and propoxylated arylalkylphenols, and also sulfated or phosphorylated arylalkylethoxylates and / or Arylalkylethoxypropoxylate, and examples include sorbitan derivatives (polyethylene oxide-sorbitan fatty acid ester, sorbitan fatty acid ester, and the like).

  For example, according to process (A), ethyl N-[(4-chloro-2,6-dimethyl) phenylacetyl] -1-amino-3-methoxycyclopentanecarboxylate can be used as a starting material for the process of the present invention. The process can be represented by the following reaction scheme.

  For example, according to process (B), using the ethyl O-[(2-chloro-6-methyl) phenylacetyl] -1-hydroxy-3-ethoxycyclopentanecarboxylate, the course of the process of the present invention is reacted as follows: It can be represented by a scheme.

  For example, starting from 7-butoxy-3-[(4-chloro-2,6-dimethyl) phenyl] -1-azaspiro [4,4] nonane-2,4-dione and pivaloyl chloride according to process (Cα) Can be used to represent the course of the process of the present invention in the following reaction scheme.

  For example, according to Process (C) (modified β), 7-ethoxy-3-[(2,4-dichloro) phenyl] -1-oxaspiro- [4,4] -nonane-2,4-dione and acetic anhydride. Used as a starting material, the course of the process of the invention can be represented by the following reaction scheme.

  For example, according to process (D), 7-methoxy-3-[(2,4-dichloro-6-methyl) -phenyl] -1-azaspiro [4,4] nonane-2,4-dione and ethyl chloroformate Used as a starting material, the course of the process of the invention can be represented by the following reaction scheme.

  For example, according to process (E), 7-ethoxy-3-[(2,4,6-trimethyl) phenyl] -1-oxa-spiro [4,4] nonane-2,4-dione and methyl chloromonothioformate Can be used as a starting material and the course of the process of the invention can be represented by the following reaction scheme.

  For example, according to process (F), starting from 7-butoxy-3-[(2,4,6-trimethyl) phenyl] -1-azaspiro [4,4] nonane-2,4-dione and methanesulfonyl chloride In use, the course of the process of the present invention can be represented by the following reaction scheme.

  For example, according to process (G), 7-methoxy-3-[(2,4-dichloro-6-methyl) -phenyl] -1-oxaspiro [4,4] nonane-2,4-dione and methanethiophosphonyl Using chloride 2,2,2-trifluoromethyl ester as a starting material, the course of the process of the present invention can be represented by the following reaction scheme.

  For example, according to process (H), 7-methoxy-3-[(2,3,4,6-tetramethylphenyl) -1-azaspiro [4,4] nonane-2,4-dione and NaOH as constituents In use, the course of the process of the present invention can be represented by the following reaction scheme.

  For example, according to process (I) (modified α), 7-ethoxy-3-[(2,4,5-trimethyl) phenyl] -1-oxaspiro [4,4] nonane-2,4-dione and ethyl isocyanate Can be used as a starting material and the course of the process of the invention can be represented by the following reaction scheme.

  For example, according to Process (I) (modified β), 7-butoxy-3-[(2,4,6-trimethyl) phenyl] -1-azaspiro [4,4] nonane-2,4-dione and dimethylcarbamoyl chloride Can be used as a starting material and the course of the process of the invention can be represented by the following reaction scheme.

  The following formula (II) required as starting material for the process (A) of the present invention:

式中、
Ａ、Ｂ、Ｑ^１、Ｑ^２、Ｗ、Ｘ、Ｙ、ＺおよびＲ^８は、上記で定義されるとおりである、
の化合物は新規である。

Where
A, B, Q ¹ , Q ² , W, X, Y, Z and R ⁸ are as defined above.
This compound is novel.

  The acylamino acid ester of the formula (II) is, for example, the following formula (XIV)

式中、
Ａ、Ｂ、Ｑ^１およびＱ^２ならびにＲ^８は、上記で定義されるとおりである、
のアミノ酸誘導体を、以下の式（ＸＶ）

Where
A, B, Q ¹ and Q ² and R ⁸ are as defined above,
Amino acid derivatives of the following formula (XV)

式中、
Ｗ、Ｘ、ＹおよびＺは、上記で定義されるとおりであり、
Ｕは、カルボニルジイミダゾール、カルボニルジイミドなどのカルボン酸活性化試薬（例えば、ジシクロヘキシルカルボジイミドなど）、ホスホリル化試薬（例えば、ＰＯＣｌ_３、ＢＯＰ−Ｃｌなど）、ハロゲン化剤（例えば、チオニルクロリド：オキサリルクロリド、ホスゲン、またはクロロギ酸エステルなど）により導入される脱離基である、
（Ｃｈｅｍ．Ｒｅｖｉｅｗｓ ５２，２３７−４１６（１９５３）；Ｂｈａｔｔａｃｈａｒｙａ，Ｉｎｄｉａｎ Ｊ．Ｃｈｅｍ．６，３４１−５，１９６８）
の置換フェニル酢酸誘導体でアシル化、または式（ＸＶＩ）

Where
W, X, Y and Z are as defined above;
U represents a carboxylic acid activating reagent such as carbonyldiimidazole or carbonyldiimide (eg, dicyclohexylcarbodiimide), a phosphorylating reagent (eg, POCl ₃ , BOP-Cl, etc.), a halogenating agent (eg, thionyl chloride: oxalyl chloride). , Phosgene, or chloroformate, etc.)
(Chem. Reviews 52, 237-416 (1953); Bhattacharya, Indian J. Chem. 6, 341-5, 1968).
With a substituted phenylacetic acid derivative of formula (XVI)

式中、
Ａ、Ｂ、Ｑ^１、Ｑ^２、Ｗ、Ｘ、ＹおよびＺは、上記で定義されるとおりである、
のアシルアミノ酸をエステル化する（Ｃｈｅｍ．Ｉｎｄ．（Ｌｏｎｄｏｎ）１５６８（１９６８））と、得られる。

Where
A, B, Q ¹ , Q ² , W, X, Y and Z are as defined above,
Is obtained by esterification (Chem. Ind. (London) 1568 (1968)).

  The following formula (XVI)

式中、
Ａ、Ｂ、Ｑ^１、Ｑ^２、Ｗ、Ｘ、ＹおよびＺは、上記で定義されるとおりである、
の化合物は新規である。

Where
A, B, Q ¹ , Q ² , W, X, Y and Z are as defined above,
This compound is novel.

  The compound of formula (XVI) is, for example, the following formula (XVII)

式中、
Ａ、Ｂ、Ｑ^１、およびＱ^２は、上記で定義されるとおりである、
の１−アミノシクロヘキサンカルボン酸を、Ｓｃｈｏｔｔｅｎ−Ｂａｕｍａｎｎ（Ｏｒｇａｎｉｋｕｍ，ＶＥＢ Ｄｅｕｔｓｃｈｅｒ Ｖｅｒｌａｇ ｄｅｒ Ｗｉｓｓｅｎ−ｓｃｈａｆｔｅｎ，Ｂｅｒｌｉｎ １９７７，ｐ．５０５）に従って、以下の式（ＸＶ）

Where
A, B, Q ¹ and Q ² are as defined above.
According to the following formula (XV)

式中、
Ｕ、Ｗ、Ｘ、ＹおよびＺは、上記で定義されるとおりである
の置換フェニル酢酸誘導体でアシル化すると、得られる。

Where
U, W, X, Y and Z are obtained upon acylation with a substituted phenylacetic acid derivative as defined above.

  Some of the compounds of formula (XV) are known and / or they can be prepared by known processes of the published publications mentioned at the beginning.

  Some of the compounds of formula (XIV) and formula (XVII) are novel and can be prepared by known processes (Tetrahedron Assembly, 8, 825 ff (1997) and WO 02/46128).

  The following formula (III) required as starting material for process (B) according to the invention:

式中、
Ａ、Ｂ、Ｑ^１、Ｑ^２、Ｗ、Ｘ、Ｙ、ＺおよびＲ^８は、上記で定義されるとおりである、
の化合物は新規である。

Where
A, B, Q ¹ , Q ² , W, X, Y, Z and R ⁸ are as defined above.
This compound is novel.

  They can in principle be prepared in a simple manner by known methods.

  The compound of formula (III) is, for example, the following formula (XVIII)

式中、
Ａ、Ｂ、Ｑ^１、Ｑ^２およびＲ^８は、上記で定義されるとおりである、
の１−ヒドロキシシクロヘキサンカルボン酸エステルを、以下の式（ＸＶ）

Where
A, B, Q ¹ , Q ² and R ⁸ are as defined above,
1-hydroxycyclohexanecarboxylic acid ester of the following formula (XV)

式中、
Ｕ、Ｗ、Ｘ、ＹおよびＺは、上記で定義されるとおりである、
の置換フェニル酢酸誘導体でアシル化すると、得られる
（Ｃｈｅｍ．Ｒｅｖｉｅｗｓ ５２，２３７−４１６（１９５３））。

Where
U, W, X, Y and Z are as defined above.
And is substituted with a substituted phenylacetic acid derivative of (Chem. Reviews 52, 237-416 (1953)).

  The 1-hydroxy-3-alkoxycyclopentyl carboxylic acid ester of the formula (XVIII) is novel. These are obtained, for example, by reacting a substituted 1-hydroxy-3-alkoxycyclopentanecarbonitrile with an alcohol in the presence of an acid, for example according to Pinner. Cyanohydrin is obtained, for example, by reacting substituted 3-alkoxycyclopentan-1-one with hydrocyanic acid.

  An acid halide of formula (IV) necessary as starting material for carrying out processes (C), (D), (E), (F), (G), (H) and (I) according to the invention, Carboxylic anhydride of formula (V), chloroformate or chloroformate thioester of formula (VI), chloromonothioformate or chlorodithioformate of formula (VII), sulfonyl chloride of formula (VIII), of formula (IX) Phosphorus compounds, and metal hydroxides, metal alkoxides or amines of formula (X) and (XI), respectively, and isocyanates of formula (XII) and carbamoyl chlorides of formula (XIII) are generally organic or inorganic chemistry. Is a known compound.

  The compounds of formula (XV) are also known from the patent applications mentioned at the outset and / or can be prepared by the methods described therein.

Process (A) is carried out in the presence of a diluent and in the presence of a base, the compounds of formula (II) (A, B, Q ¹ , Q ² , W, X, Y, Z and R ⁸ are as defined above. As defined)).

  Suitable diluents for use in the process (A) according to the invention are all organic solvents which are inert with respect to the reactants. Preferably, hydrocarbons (such as toluene and xylene), even more ethers (such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether, and diglycol dimethyl ether), and even more polar solvents (dimethyl sulfoxide, sulfolane, dimethylformamide, and N -Methylpyrrolidone etc.) as well as the use of alcohols (methanol, ethanol, propanol, isopropanol, butanol, isobutanol and tert-butanol).

Suitable bases (deprotonating agents) for use in process (A) according to the invention are all conventional proton acceptors. Preferably, the use of alkali metal and alkaline earth metal oxides, hydroxides and carbonates such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate, and calcium carbonate And these are phase transfer catalysts (eg triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464 (= methyltrialkyl (C ₈ -C ₁₀ ) ammonium chloride), or TDA1 (= tris (methoxyethoxyethyl) amine) Etc.) may be used. The use of alkali metals (such as sodium or potassium) is also possible. Further, alkali metal and alkaline earth metal amides and hydrides (such as sodium amide, sodium hydride, and calcium hydride), and alkali metal alkoxides (such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide) are also used. It is possible.

  When carrying out the process (A) according to the invention, the reaction temperatures can be varied within a relatively wide range. In general, the process is carried out between -75 ° C and 200 ° C, preferably between -50 ° C and 150 ° C.

  Process (A) is generally carried out under atmospheric pressure.

  When carrying out process (A) according to the invention, the reaction component of formula (II) and the deprotonated base are generally used in equimolar to twice the equivalent molar amount. However, it is also possible to use one component in a relatively excessive amount (up to an upper limit of 3 mol) relative to the other.

Process (B) is a compound of formula (III) (A, B, Q ¹ , Q ² , W, X, Y, Z and R ⁸ is defined above in the presence of a diluent and a base. In the molecule.

  Suitable diluents for use in process (B) according to the present invention are all organic solvents which are inert to the reactants. Preferably, hydrocarbons (such as toluene and xylene), even more ethers (such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethyl ether), even more polar solvents (dimethyl sulfoxide, sulfolane, dimethylformamide, and N- Use of methylpyrrolidone). The use of alcohols (methanol, ethanol, propanol, isopropanol, butanol, isobutanol and tert-butanol) is also possible.

Suitable bases (deprotonating agents) for carrying out the process (B) according to the invention are all usual proton acceptors. Preferred is the use of alkali metal and alkaline earth metal oxides, hydroxides and carbonates such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate and calcium carbonate. these are the phase transfer catalyst (e.g., triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464 (= methyltrialkyl _(C 8 _{-C 10)} ammonium chloride) or TDA1 (= tris (methoxyethoxyethyl) amine)) May be used in the presence of The use of alkali metals (such as sodium or potassium) is also possible. Furthermore, amides and hydrides of alkali metals and alkaline earth metals (such as sodium amide, sodium hydride and calcium hydride), and alkali metal alkoxides (such as sodium methoxide, sodium ethoxide and potassium tert-butoxide) are also used. Is possible.

  When carrying out the process (B) according to the invention, the reaction temperature can vary within a relatively wide range. In general, the process is carried out between -75 ° C and 200 ° C, preferably between -50 ° C and 150 ° C.

  Process (B) is generally performed under atmospheric pressure.

  When carrying out process (B) according to the invention, the reaction component of formula (III) and the deprotonated base are generally used in about equimolar amounts. However, it is also possible to use one component in a relatively excessive amount (up to an upper limit of 3 mol) relative to the other.

  Process (Cα) comprises the steps of formulas (I-1-a) to (I-2-a), respectively, in the presence of a diluent, if appropriate, and in the presence of an acid binder, respectively. And reacting with a carbonyl halide of the formula (IV).

  Suitable diluents for use in the process (Cα) according to the invention are all organic solvents which are inert to acid halides. Preferably, hydrocarbons (such as benzine, benzene, toluene, xylene and tetralin), even more halogenated hydrocarbons (such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene), and even more ketones (acetone). And methyl isopropyl ketone), further ethers (such as diethyl ether, tetrahydrofuran and dioxane), carboxylic acid esters (such as ethyl acetate), and also strong polar solvents (such as dimethylformamide, dimethyl sulfoxide and sulfolane). If the acid halide is sufficiently stable to hydrolysis, the reaction can be carried out in the presence of water.

  Suitable acid binders for the reaction according to the process (Cα) according to the invention are all the usual acid acceptors. Preferably, tertiary amines (such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecene (DBU), diazabicyclononene (DBN), Hunig base, and N, N-dimethylaniline), Even more alkaline earth metal oxides (such as magnesium oxide and calcium oxide), still more alkali metal and alkaline earth metal carbonates (such as sodium carbonate, potassium carbonate, and calcium carbonate), also alkali metal hydroxides (Such as sodium hydroxide and potassium hydroxide).

  The reaction temperature of the process (Cα) according to the invention can vary within a relatively wide range. In general, the process is carried out between −20 ° C. and + 150 ° C., preferably between 0 ° C. and 100 ° C.

  When carrying out the process (Cα) according to the invention, the starting materials of the formulas (I-1-a) to (I-2-a) and the carbonyl halides of the formula (IV) are generally used in approximately equal amounts, respectively. However, it is also possible to use carbonyl halide in a relatively excessive amount (up to an upper limit of 5 mol). Post-processing is performed by a normal method.

  Process (Cβ) may be carried out to convert compounds of formula (I-1-a) to (I-2-a), respectively, in the presence of a diluent, if appropriate, and in the presence of an acid binder, respectively. (V) It is made to react with carboxylic anhydride.

  Diluents suitable for use in the process (Cβ) according to the invention are preferably preferred diluents also when using acid halides. Furthermore, excess carboxylic anhydride can simultaneously act as a diluent.

  Acid binders suitable for the process (Cβ) are added if appropriate, but are also preferred acid binders when using acid halides.

  The reaction temperature of the process (Cβ) according to the invention can vary within a relatively wide range. In general, the process is carried out between −20 ° C. and + 150 ° C., preferably between 0 ° C. and 100 ° C.

  When carrying out the process (Cβ) according to the invention, the starting materials of the formulas (I-1-a) to (I-2-a) and the carboxylic anhydrides of the formula (V) are generally used in approximately equal amounts each. . However, it is also possible to use carboxylic anhydride in a relatively excessive amount (up to an upper limit of 5 mol). Post-processing is performed by a normal method.

  Generally, the diluent, excess carboxylic anhydride, and formed carboxylic acid are removed by distillation or by washing with an organic solvent or with water.

  Process (D) comprises the steps of compounds of formulas (I-1-a) to (I-2-a), respectively, in the presence of a diluent, if appropriate, and in the presence of an acid binder, respectively. Reaction with (VI) chloroformate or chloroformate thioester.

  Suitable binders for process (D) according to the invention are all the usual acid acceptors. Preferably, tertiary amines (such as triethylamine, pyridine, DABCO, DBU, DBN, Hunig base, and N, N-dimethylaniline), even more alkaline earth metal oxides (such as magnesium oxide and calcium oxide), and more Are alkali metal and alkaline earth metal carbonates (such as sodium carbonate, potassium carbonate, and calcium carbonate), and also alkali metal hydroxides (such as sodium hydroxide and potassium hydroxide).

  Suitable diluents for use in process (D) according to the invention are all solvents which are inert with respect to chloroformate or chloroformate thioester. Preferably, hydrocarbons (such as benzine, benzene, toluene, xylene, and tetralin), even more halogenated hydrocarbons (such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene, and o-dichlorobenzene), and even more ketones (Acetone and methyl isopropyl ketone), further ethers (such as diethyl ether, tetrahydrofuran, and dioxane), carboxylic acid esters (such as ethyl acetate), nitriles (such as acetonitrile), and also strongly polar solvents (dimethylformamide, Dimethyl sulfoxide and sulfolane).

  When carrying out process (D) according to the invention, the reaction temperatures can be varied within a relatively wide range. In general, the temperature is between −20 ° C. and + 100 ° C., preferably between 0 ° C. and 50 ° C.

  Process (D) according to the invention is generally carried out under atmospheric pressure.

  When carrying out process (D) according to the invention, the starting materials of formulas (I-1-a) to (I-2-a) and the appropriate chloroformate or chloroformate thioester of formula (VI) are generally Used in approximately equal amounts. However, it is also possible to use one component in a relatively excessive amount (up to an upper limit of 2 mol) relative to the other. Post-processing is performed by a normal method. In general, the precipitated salts are removed and the remaining reaction mixture is concentrated by removing the diluent under reduced pressure.

  Process (E) according to the present invention comprises compounds of formulas (I-1-a) to (I-2-a) in the presence of a diluent and, where appropriate, in the presence of an acid binder, respectively. It is made to react with the compound of (VII).

  In the preparation process (E), the chloromono of formula (VII) per mole of starting material of formula (I-1-a) to (I-2-a) at 0 to 120 ° C., preferably 20 to 60 ° C. About 1 mole of thioformate or chlorodithioformate is used.

  Suitable diluents added where appropriate are all inert polar organic solvents (ethers, amides, sulfones, sulfoxides, etc.), as well as halogenated alkanes.

  Preference is given to using dimethyl sulfoxide, tetrahydrofuran, dimethylformamide, ethyl acetate or methylene chloride.

  In a preferred embodiment, the enolate salt of (I-2-a) is prepared from compound (I-1-a) by adding a strong deprotonating agent (such as sodium hydride or potassium tert-butoxide). Further additions of acid binders may be made.

  Suitable bases for use in process (E) are all normal proton acceptors. Preferably, alkali metal hydrides, alkali metal alkoxides, alkali metal or alkaline earth metal carbonates or bicarbonates, or nitrogen bases are used. Examples include sodium hydride, sodium methoxide, sodium hydroxide, calcium hydroxide, potassium carbonate, sodium bicarbonate, triethylamine, dibenzylamine, diisopropylamine, pyridine, quinoline, diazabicyclooctane (DABCO), diazabicyclononene (DBN), and diazabicycloundecene (DBU).

  The reaction may be performed under atmospheric pressure or under pressure, and is preferably performed under atmospheric pressure. Post-processing is performed by a normal method.

  Process (F) according to the present invention comprises compounds of formulas (I-1-a) to (I-2-a), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder. Each of which is reacted with a sulfonyl chloride of the formula (VIII).

  In the preparation process (F), the sulfonyl of formula (VIII) per mole of starting material of formula (I-1-a) to (I-2-a) at −20 to 150 ° C., preferably 0 to 70 ° C. About 1 mole of chloride is reacted.

  Process (F) is preferably carried out in the presence of a diluent.

  Suitable diluents are all inert polar organic solvents (such as ethers, amides, ketones, carboxylic esters, nitriles, sulfones, sulfoxides) or halogenated hydrocarbons (such as methylene chloride).

  Preferably, dimethyl sulfoxide, tetrahydrofuran, dimethylformamide, ethyl acetate, or methylene chloride is used.

  In a preferred embodiment, the enolate salt of (I-2-a) is prepared from compound (I-1-a) by adding a strong deprotonating agent (such as sodium hydride or potassium tert-butoxide). Further additions of acid binders may be made.

  When acid binders are used, these are common inorganic or organic bases such as sodium hydroxide, sodium carbonate, potassium carbonate, pyridine and triethylamine.

  The reaction may be performed under atmospheric pressure or under pressure, and is preferably performed under atmospheric pressure. Post-processing is performed by a normal method.

  Process (G) according to the present invention comprises compounds of formulas (I-1-a) to (I-2-a) in the presence of diluents and, where appropriate, in the presence of acid binders. Each of which is reacted with a phosphorus compound of the formula (IX).

  In the preparation process (G), in order to obtain the compound of the formula (I-1-e) to (I-2-e), the compound (I-e) is used at a temperature of −40 to 150 ° C., preferably −10 to 110 ° C. 1 to 2 moles, preferably 1 to 1.3 moles of the phosphorus compound of formula (IX) are reacted per mole of 1-a) to (I-2-a).

  Process (G) is preferably carried out in the presence of a diluent.

  Suitable diluents are all inert polar organic solvents (ethers, carboxylic esters, halogenated hydrocarbons, ketones, amides, nitriles, sulfones, sulfoxides, etc.).

  Preference is given to using acetonitrile, dimethyl sulfoxide, tetrahydro, dimethylformamide, methylene chloride.

  Suitable acid binders added where appropriate are the usual inorganic or organic bases such as hydroxides, carbonates or amines. Examples include sodium hydroxide, sodium carbonate, potassium carbonate, pyridine and triethylamine.

  The reaction can be carried out under atmospheric pressure or under pressure, preferably under atmospheric pressure. The post-treatment is carried out by the usual method of organic chemistry. The final product is preferably purified by crystallization, chromatographic purification or “initiative distillation”, ie removal of volatile elements under reduced pressure.

  Process (H) comprises, if appropriate in the presence of a diluent, the compounds of formulas (I-1-a) to (I-2-a), respectively, a metal hydroxide or alkoxide of formula (X), Or it is made to react with the amine of a formula (XI).

  Suitable diluents for use in the process (H) according to the invention are preferably ethers (such as tetrahydrofuran, dioxane, diethyl ether) or alcohols (such as methanol, ethanol, isopropanol) as well as water. Process (H) according to the invention is generally carried out under atmospheric pressure. The reaction temperature is generally between −20 ° C. and 100 ° C., preferably between 0 ° C. and 50 ° C.

  Process (I) according to the invention comprises compounds of formulas (I-1-a) to (I-2-a), (Iα) in the presence of a diluent, if appropriate, and in the presence of a catalyst, if appropriate. Each with a compound of formula (XII) or (Iβ) with a compound of formula (XIII), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder. Features.

  In the preparation process (Iα), an isocyanate of formula (XII) per mole of starting material of formula (I-1-a) to (I-2-a) at 0 to 100 ° C., preferably 20 to 50 ° C. About 1 mole is reacted.

  Process (Iα) is preferably carried out in the presence of a diluent.

  Suitable diluents are all inert organic solvents such as aromatic hydrocarbons, halogenated hydrocarbons, ethers, amides, nitriles, sulfones or sulfoxides.

  If appropriate, a catalyst may be added to speed up the reaction. Highly advantageous for use as a catalyst are organotin compounds such as dibutyltin dilaurate.

  The reaction is preferably carried out under atmospheric pressure.

  In the preparation process (Iβ), the carbamoyl chloride of the formula (XIII) per mole of starting compound of the formulas (I-1-a) to (I-2-a) at 0 to 150 ° C., preferably 20 to 70 ° C. About 1 mole is reacted.

  Suitable diluents added where appropriate are all inert polar organic solvents such as ethers, carboxylic esters, nitriles, ketones, amides, sulfones, sulfoxides, or halogenated hydrocarbons.

  Preference is given to using dimethyl sulfoxide, tetrahydrofuran, dimethylformamide or methylene chloride.

  In a preferred embodiment, the enolate salt of (I-2-a) is prepared from compound (I-1-a) by adding a strong deprotonating agent (such as sodium hydride or potassium tert-butoxide). Further additions of acid binders may be made.

  If acid binders are used, these are the usual inorganic or organic bases (eg sodium hydroxide, sodium carbonate, potassium carbonate, triethylamine or pyridine).

  The reaction can be carried out under atmospheric pressure or under pressure, preferably under atmospheric pressure. Post-processing is performed by a normal method.

  The active compounds of the present invention, in combination with good plant resistance and favorable toxicity to warm-blooded animals, and less burden on the environment, protect plants and plant tissues, increase yields and improve crop quality. Improve, agriculture, horticulture, animal husbandry, forestry, garden and leisure facilities, storage and harvest protection, and pests, especially insects, arachnids, helminths found in the sanitation sector Suitable for controlling worms, nematodes, and molluscs. The active compounds according to the invention can preferably be used as plant protection agents. The active compounds of the present invention are active against normally sensitive and resistant species and are active at all or some stages of development. Examples of the harmful animals include the following.

  From the order of the lice (Anoplura / Phthiraptera), for example, Damalinia species, Haematopinus species, Linognatus species, Pediculus species, Trichodects species (Trichectes species).

  From the order of the Archnida, for example, Acarus siro, Aceria sheldoni, Aculops, Aculus, Amblyomma, Amblyomag -Boophilus species, Brevipalpus species, Bryobia praetica, Choriotes species, Dermanissus gallinae, us , Eutetranych us), Eriophyes, Hemitarsonemus, Hyalomma, Ixodes, Latrodetus mactans, Metatetray ont , Ornithodoros species, Panonychus species, Phyllocoptoruta oleivora species, Polyphagotarsoneus ruspse species, Polyphagotarsonus raspis species, Gurifusu (Rhizoglyphus) species, Sarukoputesu (Sarcoptes) species, Scorpio Maurus (Scorpio maurus), Stenotrophomonas Tal Sone Mus (Stenotarsonemus) species, Tarusonemusu (Tarsonemus) species, Tetranychus (Tetranychus) species, Basatesu-Rikoperushiki (Vasates lycopersici).

  From the order of the Bivalva, for example, the Dreissena species.

  From the order of the Chilopoda, for example, Geophilus species, Scutigera species.

  From the order of the Coleoptera, for example, Acanthoscelides obectus, Adoreticus species, Agelastica alni, Agriotis agriphytes Anobium puncatum, Anoplophora, Anthonymus, Anthrenus, Apogonia, Atomartis, Atomatius ruchidisus objectus, Bruchus species, Ceutorhynchus species, Cleonus mendicus species, Conoderus species, Cosmoelites species, Cosmopolites species, and Cosmopolites species. Cryptorhynchus lapathi, Dermestes, Diabrotica, Epilacina, Faustinus cubis, G oides), Heteronikusu-Aretoru (Heteronychus arator), Hiramorufa elegans (Hylamorpha elegans), Hirotorupesu-Bajurusu (Hylotrupes bajulus), Hipera-Posuchika (Hypera postica), Hiposenemusu (Hypothenemus) species, Rakunosuteruna-Konsanginea (Lachnosterna consanguinea), Leptinotarsa・ Desemlineata (Leptinotarsa decemlineata), Lissohoptrus oryzophilus, Lixus species, Lyctus species, Merigetes aeneus (Meliges arieth) neuus), Melolontha melolontha, Migdolus species, Monochamus species, Naupactus xanthographs, Naupactus oloteus (Noractus xanthographus) Oryzaephilus surinamensis, Othiorhinchus sulcatus, Oxycetonia jucunda, Fedon cochleon e Faga (Phyllophaga) species, Popiria-japonica (Popillia japonica), Puremunotoripesu (Premnotrypes) species, Pushiriodesu-Kurisosefara (Psylliodes chrysocephala), Puchinusu (Ptinus) species, Rizobiusu-Bentorarisu (Rhizobius ventralis), Rizoperuta-Dominican (Rhizopertha dominica), Cytophyllus species, Sphenophorus species, Sternechus species, Symphyletes species, Tenebrio molitor, Tribolium species, Trogoderma species Trogoderma species, Tychius species, Xylotrechus species, Zabrus species.

  From the order of the Collembola, for example, Onychiurus armatus.

  From the order of the Dermaptera, for example, Forficula auricularia.

  From the order of the Diplopoda, for example, Blaniulus guttulatus.

  From the order of the Diptera, for example, Aedes species, Anopheles species, Bibio hortulanus, Caliphora erythrocephala, Citita critata Species, Cochliomyia species, Cordylobia anthropofaga, Culex species, Cutterebra species, Dacus oleae, Minato a D Ophila species, Fannia species, Gastrophilus species, Hylemyia species, Hippobosca species, Hypoderma species, Liriomyza species, Liriomyzia species ) Species, Nezara species, Oestrus species, Oscineella frit, Pegomia hyoscyamii, Phorbia species, Stomata species, Stomata species (Tannia) species, Tipula paludosa, wallfall A (Wohlfahrtia) species.

  From the order of the Gastropoda, for example, Arion species, Biomphalaria species, Bulinus species, Deroceras species, Galba species, Lymnaea species, Oncomeria species, Oncomelania) species, Succinea species.

  Helminths from the eyes of (helminths), for example, Anshirosutoma-Deyuodenare (Ancylostoma duodenale), Anshirosutoma-Seiranikumu (Ancylostoma ceylanicum), Anshirosutoma brasiliensis down cis (Acylostoma braziliensis), Anshirosutoma (Ancylostoma) species, Ascaris Ruburikoidesu (Ascaris lubricoides) , Ascaris species, Brugia malaii, Brugia timori, Bunostomum species, Chabertia species, Clonorchis species, c-peria ) Species, Dicrocoelium species, Dictiocaurus filariae, Diphyllobothium diascus diascus (Echinococcus multilocularis), Enterobius vermicularis, Faciola, Haemonchus, Heterakis, Hemenolepis Nana (H menolepis nana, Hyostrongulus species, Loa Loa, Nematodilus species, Oesophagosturcium species, Opissolchus species (Ostertagia) species, Paragonimus species, Schistosomen species, Strongyloides fueleborni, Strongyloides Sterocolloidos (Strongyrodes) oides species, Tenenia saginata, Tenenia solium, Trichinella spiralis, Trichinella nachiva, Trichinella natto ), Trichinella pseudourapsis, Trichostrongulus sp., Trichris trichuria, Uchereria bancheriaf.

  It is further possible to control protozoa (such as Eimeria).

  From the order of the Heteroptera, for example, Anasa tristis, Antestiopsis, Blissus, Calocoris, Campylomaris, Species, Cimex species, Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Dikonoris derc, Helici -Skistus ( usistus species, Eurygaster species, Heliopeltis species, Horcias nobilellus species, Leptocorissa species, Leptogross philopus, Leptogloss species Exocabatus (Macropes excavatus), Miridae (Mizidae), Nezara (Nezara) species, Oebalus (Oebalus) species, Pentomidae, Puesma quadrata (Peuma quadrata), P Shi -Pseudacysta persea, Rhodnius species, Sahlbergella singularis, Scotinophora species, Stefanistobti species seed.

  From the order of the family Homoptera, for example, Acylthosipon species, Aeneolamia species, Agonoscena species, Aleurodes ur, and Aureurodes uroleo b Amrasca species, Anuraphis cardui, Aonidiella species, Aphanostigma piri, Aphis species, Arbordia apicaris (Arbidia apicaris) , Aspidiotus spp., Attanus spp., Auracorthum solai spp., Bemisia spp. Calligypona marginata, Carneocefala fulgida, Seratovacuna lanigera, Cercopiodae, Cercopidae, Cercopidae Chiffon Furagaeforii (Chaetosiphon fragaefolii), Kionasupisu-Tegarenshisu (Chionaspis tegalensis), Kurorita-Onukii (Chlorita onukii), Kuromafisu Ju Grundy Kola (Chromaphis juglandicola), chestnut Som Fars, ficus (Chrysomphalus ficus), Shikadeyurina-Mbira (Cicadulina mbila ), Coccomitilus halli, Coccus species, Cryptomiz ribis, Dalbulus species, Dialeurodes species, Diaforina (Diaforinas) aphorina species, Diaspis species, Doralis species, Drosica species, Dysapis species, Dysmicoccus species, Empoaska species, Eliosoma species Eliosoma Ura (Erythroneura) species, Eusecelis bilobatus, Geococcus coffeae, Homalodisca coagulata (Homalodisca coagulata), Hyalopters seed Idioscopus spp., Laodelphax striatellus, Lecanium spp. (Lepidaphs) spp. Melanaphis sacchari, Metcalfiella spp., Metopolophium dirhodum, Monelia costalis, Monelliopsis pecarnis Opsis pecanis, Myzus spp., Nasobia ribisnigri, Nephotetia spp. Myrtle fly (Parabemisia myricae), Paretorioza (Paratrioza), Pallateria (Pemphigus), Peregrinus maidis (Peregrinus maisu), Phenacophis cc (h) loeomyzus passerinii), Phorodon humuli, Phylloxera spp. Pseudauracapis pentagona, Pseudococcus species, Psylla species, Pteromalus species, Pyrilla species, Quadraspidiotus species, Quedada spidiotus species gigas, Rastrococcus species, Rhopalosiphum species, Saissetia species, Scaphoides titanus, Schizophis graminas Sogata species, Sogatera furcifera, Sogatades species, Stoctocefala festina, Tenaraphala maris-ensis Eforiae (Tinocallis caryaefoliae), Tomasupisu (Tomaspis) species, Tokisoputera (Toxoptera) species, Toriareurodesu-Baporariorumu (Trialeurodes vaporariorum), Torioza (Trioza) species, Chifuroshiba (Typhlocyba) species, Yunasupisu (Unaspis) species, Biteusu-Bitiforii (Viteus vitifolii ).

  From the order of the Hymenoptera, for example, a Diprion species, a Hoplocampa species, a Lasius species, a Monomorium phalaoniis, a Vespa species.

  From the order of the Isopoda, for example, Armadillidium vulgare, Oniscus asellus, Porcellio scaber.

  From the order of the Isoptera, for example, Reticulitermes species, Odontotermes species.

  From the order of the Lepidoptera, for example, Acronica major, Aedia leucomelas, Agrotis species, Alabama argylacea, Alabama argillacera Brush frog (Barathra brassicae), Buccalatrix thurberella, Bupulas pinialius, Cacoecia podana (Cacoecia poda), Capua pu a pomonella, Keimatobia burumata, Chilo species, Choristona flasfera (Christoneura fumifera), Crisia ambiguella, Quéniella (Ephestia kühniella), Euprotis chrysorhoea, Uxoa (Euxoa), Feltia (Geleria), Galleria melova (Galleria melova) , Heliothis (Heliothis) species, Hofumanofira Xu - Dosupuretera (Hofmannophila pseudospretella), Homona-Magunanima (Homona magnanima), Hiponomeuta-Padera (Hyponomeuta padella), Rafiguma (Laphygma) species, Ritokorechisu Blanc caldera (Lithocolletis blancardella), Ritofan - Lantophane antenta, Loxagrotis albicosta, Lymantria spp., Malacosoma neustria, Mamestera brastrae ssicae), Mocis repanda, Mythimna separata, Oria species, Ourema oryzae, Panolis flachia Citrulla (Phyllocnistis citrella), Pieris spp., Plutella xylostella spp., Prodenia spp., Pseudaletia spp., Pseudo indulphin plus Vilaris (Pyrausta nubilalis), Spodoptera species, Thermesia genmatalis (Thermea geimalalis), Tinea pelionella (Tinea bisiriella), Cineola biseriella (Tineola bilellus) .

  From the order of the Orthoptera, for example, Acheta domesticus, Blatta orientalis, Bratella germana, Grylotalpa, Grylotalpa. ) Species, Melanoplus species, Periplaneta americana, Sistocerca gregaria.

  From the order of the Siphonaptera, for example, Ceratophyllus species, Xenopsila cheopes.

  From the order of the Symphyla, for example, Scutigerella immaculata.

  From Thysanoptera (Thysanoptera), for example, Bariotoripusu-Biforumisu (Baliothrips biformis), En'neotoripusu-Furabensu (Enneothrips flavens), Frank Rinie La (Frankliniella) species, Heriotoripusu (Heliothrips) species, Herushinotoripusu-Femorarisu (Hercinothrips femoralis), Kakotoripusu (Kakothrips ) Species, Lipiphorotrips cruenttus, Synotrips species, Taeniotrips cardamoni, Tryps species.

  From the order of the Thysanura, for example, Lepisma saccharina.

  Examples of plant parasitic nematodes include, for example, Anguina species, Apherenchoides species, Belonoaimus species, Bursaphelenchus species, Dityrenchus dipsac, Dityrenchus dipsac, Heliocotylenchus, Heterodera, Longidorus, Meloidogyne, Pratylenchus, Radforis, Radophorus Examples include hodorus species, Tylencholhynchus species, Tylenchulus species, Tylenchus semipenetrans, and Xifinema species.

  If appropriate, the compounds according to the invention can be used at certain concentrations or application rates, such as herbicides, safeners, growth regulators or agents that improve plant properties, or microbides, such as fungicides, It can also be used as an antifungal agent, bactericidal agent, viricides (including drugs against viroids) or as an agent against MLO (mycoplasma-like microorganisms) and RLO (rickettsia-like microorganisms). If appropriate, the compounds according to the invention can also be used as intermediates or precursors for the synthesis of other active compounds.

  According to the invention, all plants and all parts of plants can be treated. In the context of the present invention, plants should be understood as meaning all plants and groups of plants, including desirable and undesirable wild plants or crop plants (including naturally occurring crop plants). Crop plants that can be obtained by normal plant breeding and optimization methods, or obtained by biotechnology and genetic engineering methods, or obtained by a combination of these methods. Often includes transgenic plants and cultivars of plants that may or may not be protected by the rights of plant breeders. Plant parts are to be understood as meaning all the above and below parts of the plant as well as organs such as buds, leaves, flowers and roots, for example leaves, needles, stems. Examples include shapes, stems, flowers, fruit bodies, fruits, seeds, roots, tubers and rhizomes. Plant parts also include harvests, as well as vegetative and reproductive tissues, such as cuttings, tubers, rhizomes, scissors and seeds.

  The treatment according to the invention of plants or plant parts with the active compounds can be carried out directly or by customary treatment methods, for example by immersion, spraying, vaporization, atomization, diffusion, application, injection, And in the case of proliferating tissues, in particular seeds, it is further carried out by applying the active compound to the surroundings of the plants or plant parts, the habitat or the storage space by applying one or more coatings.

  The active compounds of the present invention can be formulated in conventional formulations (solutions, emulsions, wettable powders, aqueous and oily suspensions, powders, dusts, pastes, soluble powders, soluble granules, spraying). Granule, suspension emulsion concentrate, natural material impregnated with active compound, synthetic material impregnated with active compound, fertilizer, and microencapsulated in polymer substance).

  These formulations are prepared by known methods, for example by mixing the active compound with a bulking agent which is a liquid solvent and / or a solid carrier, and optionally a surfactant which is an emulsifier and / or dispersant and / or foam former. An agent is also used for manufacturing. The formulation is either prepared in a suitable plant or prepared before or during spraying.

  Suitable for use as auxiliaries are specific properties (some technical properties and / or specific properties) of the composition itself and / or formulations derived therefrom (eg sprays, seed dressings). It is a substance suitable for imparting biological properties. Typical suitable auxiliaries are bulking agents, solvents and carriers.

  Suitable bulking agents are, for example, water, polar and non-polar organic chemical liquids such as aromatic and non-aromatic hydrocarbons (paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes, etc.), alcohols and polyols (if appropriate) Substituted, etherified and / or esterified), ketones (acetone, cyclohexanone, etc.), esters (including fats) and (poly) ethers, unsubstituted and substituted amines, amides, lactams (N-alkyls) Pyrrolidone and the like) and lactones, sulfones, and sulfoxides (such as dimethyl sulfoxide).

  When the extender used is water, for example, an organic solvent can be used as an auxiliary solvent. In essence, suitable liquid solvents are aromatic compounds (such as xylene, toluene, or alkylnaphthalene), chlorinated aromatic and chlorinated aliphatic hydrocarbons (such as chlorobenzene, chloroethylene, or methylene chloride), aliphatic hydrocarbons (Cyclohexane or paraffins such as petroleum fractions, mineral and vegetable oils), alcohols (such as butanol or glycol) and their ethers and esters, ketones (such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone), strong polar solvents (dimethyl) Sulfoxide, etc.), as well as water.

Suitable solid carriers are
For example, ammonium salts, and ground natural minerals (kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite, or diatomaceous earth), and ground synthetic minerals (highly dispersible silica, alumina and silicates); granules Suitable solid carriers for the agent include, for example, natural rocks (calcite, marble, pumice, gypsum, and dolomite) that have been crushed and separated, and synthetic granules composed of inorganic and organic coarse powders, and organic materials (paper , Sawdust, coconut shell, corn cob, and tobacco petiole, etc.); suitable emulsifiers and / or foam formers are, for example, nonionic and anionic emulsifiers (polyoxyethylene fatty acid esters, poly Oxyethylene aliphatic alcohol ethers such as alkylaryl polyglycols Ethers, alkyl sulphonates, alkyl sulphates, aryl sulphonates, etc.), also protein hydrolysates, etc .; suitable dispersing agents are non-ionic and / or ionic substances such as alcohol-POE- and / or POP-ethers, acids and / or POP-POE esters, alkylaryls and / or POP-POE ethers, fat-and / or POP-POE adducts, POE- and / or POP-polyol derivatives, POE- and And / or POP-sorbitan- or sugar adducts, alkyl or aryl sulfates, alkyl or aryl sulfonates, and alkyl or aryl phosphates, or the corresponding PO-ether adducts. Furthermore, suitable oligos or polymers are derived, for example, from vinyl monomers, those derived from acrylic acid, EO and / or PO alone or in combination with, for example, (poly) alcohols or (poly) amines. To do. It is also possible to use lignin and its sulfonic acid derivatives, unmodified and modified cellulose, aromatic and / or aliphatic sulfonic acids and their formaldehyde adducts.

  Tackifiers such as carboxymethylcellulose, and natural and synthetic polymers (such as gum arabic, polyvinyl alcohol and polyvinyl acetate) in the form of powders, granules or latex, and natural phospholipids (such as cephalin and lecithin), And synthetic phospholipids and the like can be used in the formulation.

  Colorants such as inorganic pigments (iron oxide, titanium oxide, and Prussian blue), and organic dyes (such as alizarin dyes, azo dyes, and metal phthalocyanine dyes), and micronutrients (iron salts, manganese salts, boron salts) , Copper salts, cobalt salts, molybdenum salts, and zinc salts, etc.) can be used.

  Other possible additives are perfumes, minerals or plants, optionally modified oils, waxes and nutrients (including micronutrients) such as iron salts, manganese salts, boron salts, copper salts, cobalt salts, Molybdenum salts and zinc salts.

  Stabilizers such as low temperature stabilizers, preservatives, antioxidants, light stabilizers, or other agents that improve chemical and / or physical stability may also be present.

  The formulations generally contain between 0.01% and 98% by weight of active compound, preferably between 0.5% and 90%.

  The active compounds according to the invention can be used in this commercial preparation or other active compounds (insecticides, attractants, sterilants, fungicides, mite control agents, nematicides, fungicides, growth regulators) , Herbicides, safeners, fertilizers or information substances, etc.) and can also be used in the form of use prepared from such commercial preparations.

Particularly preferably mixed components are, for example, the following compounds.
Fungicides:
Inhibitors of nucleic acid synthesis
Benalaxyl, Benalaxyl-M, Bupirimate, Chiralaxyl, Clozilacon, Dimethylrimol, urilimol, ethirimol, ethirimol, ethirimol Metalaxyl, metalaxyl-M, oflace, oxadixyl, oxolinic acid
Inhibitors of mitosis and cell division
Benomyl, carbendazim, dietofencarb, fuberidazole, pencycuron, thiabendazole, thiabandole
Inhibitor of respiratory chain complex I
Diflumetrim
Inhibitor of respiratory chain complex II
Boscalid, carboxin, fenfuram, flutolanil, furametopyr, mepronil, oxycarboxin, penthipyrad
Inhibitor of respiratory chain complex III
Azoxystrobin, cyazofamid, dimoxystrobin, enestrobin, famoxadone, fenamidone, fluoxastrobine, fluoxastrobin (lu) , Minominostrobin, oryastrostrobin, pyraclostrobin, picoxystrobin, trifloxystrobin
Decoupler
Dinocap, fluazinam
Inhibitor of ATP production
Fentin acetate, fentin chloride, fentin hydroxide, silthiofam
Inhibitors of amino acid biosynthesis and protein biosynthesis
Andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate, mepanipyrim, pyrimethaniil
Inhibitors of signal transduction
Fenpiclonil, fludioxonil, quinoxyfen
Inhibitors of lipid and membrane synthesis
Clozolinate, iprodione, procymidone, vinclozolin
Ampropylphos, potassium-ampropylphos, edifenphos, iprobenfos (IBP), isoprothiolane, pyrazophos
Tolclofos-methyl, biphenyl
Yoodocarb, propamocarb, propamocarb hydrochloride
Inhibitors of ergosterol biosynthesis
Fenhexamide,
Azaconazole, bittertanol, bromconazole, cyproconazole, diclobutrazol, difenoconazole, difenoconazole, difenoconazole, difenoconazole, difenoconazole. epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriazole, urconazole, urconazole. Fluconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, microbutanil, polobutrazol Prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimethonone, triadimenol Riticonazole, uniconazole, voriconazole, imazaril, imazalyl sulfate, oxpoconazole, flurimol, fenarimol Pyrifenox, triforine, pefurazoate, prochloraz, triflumizole, viniconazole
Aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph, fenpropidin, spiroxamine,
Naftifine, pyributicalb, terbinafine
Inhibitors of cell wall synthesis
Benthiavaricarb, bialafos, dimethomorph, flumorph, iprovalicalb, polyoxin, polyoxolimymoloximycin
Inhibitors of melanin biosynthesis
Capropamid, diclocymet, phenoxanil, phthalide, pyroquilon, tricyclazole
Resistance inducers
Acibenzoral-S-methyl, probenazole, thiadinil
Multisite action
Captafol, captan, chlorothalonil, copper salts (such as copper hydroxide, copper naphthenate, basic copper chloride, copper sulfate, copper oxide, copper oxine, and Bold-mix), diclofluuride (Diclofluandid), dithianon, dodine, dodine free base, felbam, folpet, fluorophorpet, guazatine, guazatine acetate, iminotazine (in) Albesylate, iminoctadine triacetate, mancopper, mancozeb, mannebu b), metiram (metiram), metiram zinc, propineb (propineb), sulfur and calcium polysulfide containing sulfur preparations, thiram (thiram), tolylfluanid (tolylfluanid), zineb (zineb), ziram (ziram)
Unknown mechanism
Amibromdol, Benthiazol, Betoxazine, Capsimycin, Carvone, Quinomethionyl, Chlopicrin, Chloropicrin, Chloropicrin , Dazomet, debacarb, diclomezine, dichlorophen, dichloran, difenzoquat, difenzoquat methylsulfate, diphenylamine, Thaboxam, ferimzone, flumetover, flusulfamide, fluopicolide, fluoroimide, hexachlorobenzene, 8-hydroxy-quinoline sulfate, ilmmasulfuryl methasulfocarb, metraphenone, methyl isothiocyanate, mildiomycin, natamycin, nickel dimethyldithiocarbamate, nitrothal-isopropyl, octylone e Carbamocarb, oxyfenthiin, pentachlorophenol and salt, 2-phenylphenol and salt, piperalin, propanosine-sodium, proquinazid, pyrrolintoline, pyrrolinol (Quintozene), teclophthalam, technazene, triazoxide, trichlamide, zalamide, and 2,3,5,6-tetrachloro-4- (methylsulfonyl) pyridine, -(4-Chloro-2-nitrophenyl) -N-eth 4-methylbenzenesulfonamide, 2-amino-4-methyl-N-phenyl-5-thiazolecarboxamide, 2-chloro-N- (2,3-dihydro-1,1,3-trimethyl-1H-indene -4-yl) -3-pyridinecarboxamide, 3- [5- (4-chlorophenyl) -2,3-dimethylixazolidin-3-yl] pyridine, cis-1- (4-chlorophenyl) -2- (1H -1,2,4-triazol-1-yl) cycloheptanol, 2,4-dihydro-5-methoxy-2-methyl-4-[[[[[1- [3- (trifluoromethyl) phenyl] ethylidene ] -Amino] oxy] methyl] phenyl] -3H-1,2,3-triazol-3-one (185336-79-2), methyl 1- (2,3-dihydro-2,2 Dimethyl-1H-inden-1-yl) -1H-imidazole-5-carboxylate, 3,4,5-trichloro-2,6-pyridinedicarbonitrile, methyl 2-[[[cyclopropyl [(4-methoxy Phenyl) imino] methyl] thio] methyl] -α- (methoxymethylene) benzacetate, 4-chloro-α-propynyloxy-N- [2- [3-methoxy-4- (2-propynyloxy) phenyl] ethyl] Benzacetamide, (2S) -N- [2- [4-[[3- (4-Chlorophenyl) -2-propynyl] oxy] -3-methoxyphenyl] ethyl] -3-methyl-2-[(methylsulfonyl) ) Amino] butanamide, 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) [1 2,4] triazolo [1,5-α] pyrimidine, 5-chloro-6- (2,4,6-trifluorophenyl) -N-[(1R) -1,2,2-trimethylpropyl]-[ 1,2,4] triazolo [1,5-α] pyrimidin-7-amine, N- [1- (5-bromo-3-chloropyridin-2-yl) ethyl] -2,4-dichloronicotinamide, N- (5-bromo-3-chloropyridin-2-yl) methyl-2,4-dichloronicotinamide, 2-butoxy-6-iodo-3-propylbenzopyranon-4-one, N- { (Z)-[(Cyclopropylmethoxy) imino] [6- (difluoromethoxy) -2,3-difluorophenyl] methyl} -2-benzacetamide, N- (3-ethyl-3,5,5-trimethylcyclohexyl) ) -3-Hol Ruamino-2-hydroxybenzamide, 2-[[[[[1- [3- (1-fluoro-2-phenyl-ethyl) oxy] phenyl] ethylidene] amino] oxy] methyl] -α- (methoxyimino) -N -Methyl-αE-benzacetamide, N- {2- [3-chloro-5- (trifluoromethyl) pyridin-2-yl] ethyl} -2- (trifluoromethyl) benzamide, N- (3 ′, 4 '-Dichloro-5-fluorobiphenyl-2-yl) -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, N- (6-methoxy-3-pyridinyl) cyclopropanecarboxamide, 1- [(4-Methoxyphenoxy) methyl] -2,2-dimethylpropyl-1H-imidazole-1-carboxylic acid, O- [1-[(4-metho Ciphenoxy) methyl] -2,2-dimethylpropyl] -1H-imidazole-1-carboxylic acid, 2- (2-{[6- (3-chloro-2-methylphenoxy) -5-fluoropyrimidine-4- Yl] oxy} phenyl) -2- (methoxyimino) -N-methylacetamide
Fungicide:
Bronopol, dichlorophen, nitrapirin, nickel dimethyldithiocarbamate, kasugamycin, octylinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, copper teclophthalam, etc. Formulation.
Insecticide / Tick control / nematicide:
Acetylcholinesterase (AChE) inhibitor
Carbamate,
For example, aranicarb, aldicarb, aldoxycarb, allycarb, aminocarb, bendiocarb, benfurcarb, benfurcarb Carboxyl, butoxycarboxy, carbaryl, carbofuran, carbosulfan, cloethocarb, dithiolan (di) fencarb, fenobucarb, fenothiocarb, formatenate, furathiocarb, isoprocarb, methythiomeb, metam sodium, metam sodium (Metolcarb), oxamyl (oxamyl), pirimicarb, promecarb, propoxur, thiodicarb, thiophanox, trimetathalx, trimetacarb, x lylcarb), Toriazame - door (triazamate)
Organophosphorus,
For example, acephate azamethiphos, azinphos (-methyl, -ethyl), bromophos-ethyl, bromfenvinfos (-methyl), butathiofos (butathiofos) , Cadusafos, carbophenothion, chlorethoxyphos, chlorfenvinphos, chlormefos, chlorpyrifos (-), methylpyrifos (-) Cyanofenphos ), Cyanophos, chlorfenvinphos, demeton-S-methyl, demeton-S-methylsulfone, dialifos, diazinon, diclofenthion, dichlorvos / DDVP (Dichlorvos / DDVP), dicrotophos, dimethoate, dimethylvinphos, dioxabenfos, disulfoton, EPN, ethion, ethion, ethion. Etrimfos, femfull ( amphur, fenamifos, fenitrothion, fensulfothion, fenthion, flupyrazofos, fonothios, formothion, formothion Heptenophos, iodofenphos, iprobenfos, isazofos, isofenphos, isopropyl O-salicylate, isoxathion, malathion, melatham ecarbam, methacrifos, methamidophos, metidathion, mevinphos, monocrotophos, naledo, oxymethoet et al. , Parathion (-methyl / -ethyl), phenate, pholate, fosalone, phosmet, phosphamidon, phosphocarb, phoxim (phox) ), Pirimiphos s) (-Methyl / -ethyl), Profenofos, Propafos, Propetamfos, Prothiofos, Prothofoto, Pyraclofosid, Pyidafenthion p ), Quinalphos, cebufos, sulfotep, sulprofos, tebupyrimfos, temefos, terbufos, tetrachlorphos hiometon), triazophos (triazophos), trichlorfon (triclorfon), vamidothion (vamidothion)
Sodium channel regulator / voltage-dependent sodium channel blocker
Pyrethroid,
For example, acrinathrin, allethrin (d-cis-trans, d-trans), β-cyfluthrin, bifenthrin, bioallethrin, cycloalthrin, cycloalpentyl, S-isomer Bioethanomethrin, biopermethrin, bioresmethrin, clovaportrin, cis-cypermethrin, cis-cypermethrin, cis-cypermethrin, cis-cypermethrin, cis-cypermethrin -Permethr n), crocitrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin (α-, β-, θ-, ζ-), cyphenothrin, deltamethrin (del), deltamethrin (del) Empentrin (1R isomer), esfenvalerate, ethofenprox, fenfluthrin, fenpropathrin, fenpyritrin-, fenpyritrin (Feverate), flubrocytrinate Flucitrinate, flufenprox, flumethrin, fluvalinate, fubufenprox, γ-cyhalothrin, imiprothrin, λdeprothrin, λ , Methfluthrin, permethrin (cis-, trans-), phenothrin (1R-trans-isomer), praletrin, profluthrin, protrifenbutreprotrite (s) , Resmet , RU15525, silaflufen, τ-fulvalineate, tefluthrin, teralethrin, tetramethrin (-1R-isomer), tralomethrin (in), transfluthrin (in), ns 8901, pyrethrin (pyrethrum)
DDT
Oxadiazine series
For example, indoxacarb
Semicarbazone series
For example, metaflumizone (BAS 320l)
Acetylcholine receptor agonist / antagonist
Chloronicotinyl system
For example, acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiacloprid
Nicotine, bensultap, cartap
Acetylcholine receptor modulator
Spinosyn system,
For example, spinosad
GABA-regulated chloride channel antagonist
Organic chlorine,
For example, camphechlor, chlordane, endosulfan, γ-HCH, HCH, heptachlor, lindane, methoxychlor
Fiprole system,
For example, acetoprole, etiprole, fipronil, pyrafluprole, pyriprole, vaniliprole
Chloride channel activator
Mectin,
For example, avermectin, emamectin, emamectin benzoate, ivermectin, milbemycin
Juvenile hormone mimetic
For example, diophenolan, epofenonane, phenoxycarb, hydroprene, kinoprene, methoprene, pyriproxirene, pyriprofenne
Ecdysone agonist / breaking agent
Diacylhydrazine,
For example, chromafenozide, halofenozide, methoxyphenozide, tebufenozide
Chitin biosynthesis inhibitor
Benzoylurea,
For example, bistrifluron, clofluazuron, diflubenzuron, fluazuron, flucloxuron, flufenoxuron, flufenoxuron, flufenoxuron, flufenoxuron, flufenoxuron , Novaluron, noviflumuron, penfluron, teflubenzuron, triflumuron
Buprofezin
Cyromazine
Oxidative phosphorylation inhibitor, ATP disruptor
Diafenthiuron
Organotin compounds,
For example, azocyclotin, cyhexatin, phenbutaine oxide
Oxidative phosphorylation decoupler acting by interrupting the H-proton gradient
Pyrrole,
For example, chlorfenapyr
Dinitrophenol
For example, binapacyl, dinobuton, dinocup, DNOC
I-side (Side-I) electron transfer inhibitor
METl system,
For example, fenazaquin, fenpyroximate, pyrimidifene, pyridaben, tebufenpyrad, tolfenpyrad
Hydramethylnon
Dicofol
II side (Side-II) electron transfer inhibitor
Rotenone
III-side (Side-III) electron transfer inhibitor
Acequinocyl, fluacrylpyrim
Insect gut microbiology
Bacillus thuringiensis strain
Lipid synthesis inhibitor
Tetronic acid system,
For example, spirodiclofen, spiromesifen
Tetramic acid,
For example, spirotetramat
Carboxamides,
For example, flonicamid
Octopaminergic agonist
For example, amitraz
An inhibitor of ATPase stimulated by magnesium,
Propargite
Ryanodine receptor agonists (effectors)
a) Dicarboxamide benzoate,
For example, fulvendiamide
b) anthranilamides, for example
Rinaxapyr (3-bromo-N- {4-chloro-2-methyl-6-[(methylamino) carbonyl] phenyl} -1- (3-chloropyridin-2-yl) -1H-pyrazole-5 -Carboxamide)
Nereistoxin analogues,
For example, thiocyclam hydrogen oxalate, thiosultap-sodium
Biologics, hormones, or pheromones
Azadirachtin, Bacillus species, Beauveria species, Codremone, Metarhidium species, Paecilomyces species, uringi thium urinum )seed
Active compounds with unknown or unclear mechanism of action
Fumigant,
For example, aluminum phosphide, methyl bromide, sulfuryl fluoride
An eating inhibitor,
For example, cryolite, flonicamid, pymetrozine
Tick growth inhibitor,
For example, clofentezine, etoxazole, hexythiazox
Amidoflumet, benclothiaz, benzoximate, biphenazate, bromopropyrate, buprofezin, ro-chloro-di, Picrine, Clothiazoben, Cycloprene, Cyflumetofen, Dicyclanil, Fenoxacrim, Fentrifanil, flubenzimine , Flufenerim, flutenzin, gossyplure, hydramethylnon, japonilure, methoxadiazone, petroleum, piperonyl butoxide, sulfidyl, id (Tetradiffon), tetrasal (trirasul), trialatene, berbutin

  Mixtures with other known active compounds (herbicides, fertilizers, growth regulators, safeners, informational substances etc.) or in any case with mixtures to improve plant properties are also possible.

  When used as insecticides, the active compounds according to the invention can also be present in this commercial formulation or in a use form prepared from such a commercial formulation as a mixture with synergistic agents. A synergistic agent is a compound that increases the action of an active compound of the present invention without requiring the addition of a synergistic agent to activate itself.

  When used as insecticides, the active compounds according to the invention can also be present in this commercial preparation or in a use form prepared from such a commercial preparation as a mixture with inhibitors. Inhibitors reduce the degradation of the active compound after use in the environment surrounding the plant, or on the surface of plant parts or in plant tissues.

  The active compound content of the use forms prepared from the commercial preparations can vary within wide limits. The active compound concentration of the use forms is 0.00000001 to 95% by weight, preferably 0.00001 to 1% by weight of active compound.

  The compounds are used in a conventional manner as appropriate to the use form.

  As already mentioned above, it is possible to treat all plants and plant parts according to the invention. In preferred embodiments, wild and cultivated plant species, or those obtained by conventional biological breeding methods (such as cross or protoplast fusion), and portions thereof are treated. In a further preferred embodiment, transgenic plants, cultivated plant species obtained by genetic engineering methods (if appropriate, in combination with conventional methods (genetically modified organisms)), as well as parts thereof, are treated. The The terms “parts”, “parts of plants” and “plant parts” have been explained above.

  Particularly preferably, plants of the cultivated plant species that are commercially available or used in any case are treated according to the invention. Cultivated plant species should be understood to mean plants having novel properties (“traits”) obtained by conventional breeding, mutagenesis, or recombinant DNA techniques. The trait can be cultivated species, biotype, or genotype.

  Depending on the plant species or cultivated plant species, their habitat and growth conditions (soil, climate, vegetation period, diet), the treatment according to the invention is superadditive (“synergistic”). ) It can also have an effect. Thus, for example, reducing the spread rate and / or expanding the activity spectrum and / or increasing the activity of the substances and compositions that can be used according to the invention, improving the growth of plants, improving the tolerance to high or low temperatures, Increased tolerance to drought or water or soil salt concentrations, improved flowering performance, easier harvesting, accelerated maturity, increased yield, improved crop quality and / or improved nutritional value, storage It is possible to improve the stability and / or the processability of the harvest, which actually exceeds the expected effect.

  Preferably, as a transgenic plant or cultivated plant species (obtained by genetic engineering) to be treated according to the invention, genetic material that, by virtue of genetic modification, imparts particularly advantageous useful traits to such plants is received. All of the plants that are included. Examples of such traits include better plant growth, increased resistance to high or low temperatures, increased resistance to drought or water or soil salt concentrations, improved flowering performance, easier harvesting, maturation Acceleration, yield increase, crop quality improvement and / or nutritional value, storage stability and / or crop processability. Further and particularly emphasized as examples of such traits are better protection of plants against harmful animals and harmful microorganisms (such as insects, ticks, phytopathogenic fungi, bacteria and / or viruses), as well as against some herbicidal active compounds This is an improvement in plant tolerance. Examples of transgenic plants that may be mentioned include important crops (cereals (wheat, rice), corn, soybeans, potatoes, sugar beets, tomatoes, beans and other vegetable species, cotton, tobacco, rape, etc.) and fruits There are plants (along with apples, pears, citrus fruits and grapes), with particular emphasis on corn, soybeans, potatoes, cotton, tobacco and rape. The traits highlighted are in particular toxins formed in plants, in particular Bacillus thuringiensis (eg CryIA (a), CryIA (b), CryIA (c), CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb , And CryIF, and combinations thereof) by insects, spiders, nematodes, and slugs and by toxins formed in plants (hereinafter referred to as “Bt plants”) by genetic material from This is an improvement in plant defense against snails. Traits that are also particularly emphasized are plant resistance to fungi, bacteria, and viruses due to systemic acquired resistance (SAR), cystemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins. It is improvement of defense. A trait that is even more particularly emphasized is an increase in plant tolerance to certain herbicidally active compounds such as imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg the “PAT” gene). The gene imparting the desired trait can also be present in combination with each other in the transgenic plant. Examples of “Bt plants” that may be mentioned include corn varieties, cotton varieties, soybean varieties and potato varieties, which are sold under the following trade names: YIELD GARD® (eg, corn, cotton soybean), KnckckOut® (eg, corn), StarLink® (eg, corn). Bollgard® (cotton), Nucotn® (cotton), and NewLeaf® (potato). Examples of herbicide-tolerant plants that may be mentioned include corn varieties, cotton varieties and soybean varieties, which are sold under the following trade names: Roundup Ready® (glyphosate resistant, eg corn, cotton, soybean), Liberty Link® (phosphinotricin resistant, eg rape), IMI® (imidazolinone resistant), and STS® (sulfonylurea resistant, eg corn). Examples of herbicide-resistant plants that can be cited (plants bred in a conventional manner for herbicide resistance) include varieties sold under the following trade names: Clearfield® (eg, corn). Of course, such statements also apply to cultivated plant species having these genetic traits or those still in development, and these cultivated plant species will be developed and / or marketed in the future.

  The listed plants can be treated according to the invention in a particularly advantageous manner with the compounds of the general formula (I) and / or the active compound mixtures according to the invention. The preferred ranges described above for the active compounds or mixtures also apply to the treatment of such plants. Of particular emphasis is the treatment of plants with the compounds or mixtures specifically described herein.

  The active compounds according to the invention are not only for harmful animals in plants, hygiene products and storage, but also in animal parasites (ectoparasites and endoparasites) (hard mites, soft mites, mite mites), It is also effective in the veterinary sector of spider mites, flies (biting and licking), parasitic fly larvae, lice, lice, lice and fleas). Examples of such parasites include:

  From the order of the Anoplrida, for example, Haematopinus species, Rinognus species, pedicles species, Phtyrus, and Nolenotes species.

  From the order of Mallophagida, and Amblycerina and Ischnocerina, for example, Trimenopon species, Menopon species, Trinoton species, Trinoton species, Trinoton species, Trinoton species Wernekiella species, Lepikentron species, Damalina species, Trichodictes species, Felicola species.

  From the order of the flies, Nematocerina and Brachycerina, for example, Aedes, Anoferes, Curex, Simulium, Eusimulium, Phlebotomus Species, Lutzomyia species, Clicoides species, Chrysops species, Hybomitra species, Atylotus species, Tabanus species, Haematopato species, Haematopota species ) Species, Musca species, Hydrotaea species, Stomoxis species, Haematvia (Haemat) bia species, Morelia species, Fannia species, Grossina species, Califora species, Lucyria species, Chrysomia species, Wal-Halcia species, Sarcophaga species, Oestrus species, Hipoderma species, Gasterophilus species, Hippobosca species, Lipoptena species, Melophagas species.

  From the order of the Siphonaptida, for example, the Pulex species, the Ctenocephalides species, the Xenopsylla species, and the Seratefilus species.

  From the order of the Heteropterida, for example, Chimex species, Triatoma species, Rhodonius species, Panstrungylus species.

  From the order of the Blattida, for example, Blatta Orientalis, Periplaneta americana, Braterra Germanica, Superella species.

  From the order of the mites (Acari (Acarina)), and from the order of the tick (Metastigmata) and the subcariform (Mesostigmata), for example, Argus, Ornithodorus, Otobius, Ixodes, Ambroma Filus species, Dermacentor species, Haemophyalis species, Hyroma species, Lipipesphalus species, Dermanissus species, Lailirieia species, Pneumonysno species, Sterus species Varroa species.

  From the order of Actinidadidae (Actinedida (Prostigmata)) and Acariidae (Acarididae) (Acaridada (Astigmata)), for example, Acarapis species, Cheylettiella thiae, Ornitoles Species, Myobia species, Psorgates species, Demodex species, Trombicula species, Listrophorus species, Acarus species, Tyrophagus species, Tyrophagus species Caloglyphus species, Hypodectes species, Pterolix (Pte Olichus) species, Pusoroputesu species, Korioputesu species, Otodekutesu (Otodectes) species, Sarukoputesu species Notoedoresu (Notoedres) species, Kunemidokoputesu (Knemidocoptes) species, Shitojitesu (Cytodites) species, and Raminoshioputesu (Laminosioptes) species.

  The active compounds of the formula (I) according to the invention are agriculturally productive livestock (eg cattle, sheep, goats, horses, pigs, donkeys, camels, buffalos, rabbits, chickens, turkeys, ducks, geese and honeybees), etc. Also suitable for controlling arthropods parasitizing other pets (eg dogs, cats, eagle birds and fish tanks) and so-called test animals (eg hamsters, guinea pigs, rats, and mice) ing. By controlling such arthropods, the deaths of the animals and the decline in productivity (meat, milk, wool, leather, eggs, honey, etc.) are reduced, and therefore the active compounds according to the invention are used. Thus, a more economical and easier livestock industry is possible.

  The active compounds according to the invention are administered in a known manner in the veterinary field and in the animal industry in the manner of enteral administration (eg tablets, capsules, doses, drops, granules, pastes, bolus, feedthrough process and By parenteral administration (in the form of suppositories, etc.) (for example, injection (intramuscular injection, subcutaneous injection, intravenous injection, intraperitoneal injection, etc.), implant), intranasal administration, skin By using above (for example in the form of medicinal baths or baths, jetting, pouring and spotting, washing, and powdering) and molded articles containing the active compound (collars, Using ear tags, tail marks, limb bands, end ropes, marking devices, etc.) The

  When used in cattle, poultry, pets, etc., the active compound of formula (I) is a formulation containing an active compound in an amount of 1% to 80% by weight (eg powders, emulsions, free flowing compositions). (Free-flowing compositions)) can be used directly or diluted 100-fold to 10,000-fold, or they can be used as a chemical bath.

  Furthermore, it has been found that the compounds according to the invention show a strong insecticidal activity against insects that destroy industrial materials.

The following insects may be mentioned by way of example and as preferred but not in any way limiting:
Beetles, for example, Hirotorpes bajulus, Chlorophorus pirosis, Anovium puntactum, Xestobium rubinobum, Petulinus pectornis (Pticorn) mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus praniculis, Lyctus praniculis yctus linearis), Lyctus pubescens, Trogoxylon aequare, Mintes rugicos species, Xyrebord species Bostrychus capucins, Heterobostrus bruneus, Sinoxylon species, and Dinoderus minutus;
Hymenoptera, for example, Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, and Urocerus augur;
Termites, for example, Carotermes flavicollis, Cryptothermes brevis, Heterotermes indicola, Reticulitermes critices, Reticulitermes , Reticulitermes lucifugus, Mastothermes darwiniensis, Zoothermosis nevadensis, and Coptote Female Formosa Taunus (Coptotermes formosanus);
Spots, such as Lepisma saccharina.

  In the context of the present invention, industrial materials are lifeless materials, preferably plastics, adhesives, sizes, paper and cardboard, leather, wood and processed wood products, and coating compositions. Should be understood as meaning.

  The ready-to-use composition may contain additional insecticides if appropriate, and may contain one or more fungicides if appropriate.

  For possible further additives, reference may be made to the insecticides and fungicides mentioned above.

  The compounds according to the invention can likewise be used to protect those in contact with salt water or fresh salt water (hulls, lattices, nets, structures, mooring equipment, signaling systems, etc.) from fouling. Can do.

  Furthermore, the compounds according to the invention can be used alone or in combination with other active compounds as antifouling agents.

  In domestic, hygiene and storage protection, the active compounds are also suitable for the control of harmful animals, in particular insects, arachnids and ticks. Such animals are found, for example, in closed spaces such as homes, large factory spaces, offices, and vehicle interiors. The active compounds can be used alone or in combination with other active compounds and auxiliaries in household insecticide products that control such pests. The active compounds are effective against effective and resistant species and against all developmental stages. Examples of such harmful animals include the following.

  From the order of the Scorpionide, for example, Butus occitanus.

  From the order of the mites, for example, Argas persicus, Argas reflexus, Briobia spp. Rhipicephalus sanguineus, Trombicula alfredezgei, Neutrombicula autumnalis, Dermatophateridum tergomidos ssimus), Dermatophagoides forinae.

  From the order of the Araneae, for example, Avicularidae, Araneidae.

  From the order of the Opiumes, for example, Pseudocorpiones chelifer, Pseudocorpiones cheiridium, Opiliones phalangium.

  From the order of the Paramecium, for example, Onyx Ascerus, Porcelio Scavelle.

  From the order of the millipede, for example, Braniurus Gutzrats, Polydesmus species.

  From the order of the Centipede class, for example, Geophilus species.

  From the order of the Zygentoma, for example, Ctenolepisma species, Lepisma sacarina, Lepismodes inquilinus.

  From the order of the cockroach (Blattaria), for example, Bratta orientalis, Bratella germanica, Bratella asahinai, Leucofaea maderae, Panchora species, Parcobrata species, Parcobrata species Periplaneta australasiae, Periplaneta americana, Periplaneta brunnea, Periplaneta friginosa, Spella longipalpa.

  From the leaping eye (Saltatoria), for example, Aketa Domestics.

  From the order of the earwig, for example, Horficula auriclaria.

  From the order of the termites, for example, Carotermes species, Reticlitermes species.

  From the order of the Psocoptera, for example, Lepinatus species, Liposcelis species.

  From the order of the Coleoptera, for example, Anthrenus, Attagenus, Delmestes, Latheticus oryzae, Necrobia, Petnus, Rhizoperta dominica, Sitofilus glandus (Sitophilus oryzae), Citophilus zeamais, Stegobium paniceum.

  From the order of flies, for example, Aedes aegypti, Aedes albopictus, Aedes taeniolinkus, Anopheles species, C Culex equaciatus, Culex pipiens, Culex tarsalis, Drosophila species, Fannia canicularis, Musca dous mess Sarukofaga-Karunaria (Sarcophaga carnaria), Shimuriumu species, Sutomokishisu-Cal transfected (Stomoxys calcitrans), Chipura-Parudosa.

  From the order of the order Lepidoptera, for example, Acroia grisella, Galleria melonella, Prodia interpuntella, Tinea cloacella, Tinea pelionella, Cineola vicelliella.

  From the order of fleas, for example, Ctenocephalides canis, Ctenocephalides ferris, Plexex irritans, Tunga penetrances, Tunga penetrances.

  From the order of the bees, for example, Camponotus herculaneus, Lasius fliginosus, Lasius niger, Lasius umbratus, Lasius umbratus, Lasius umbratus, Lasius umbratus, Tetramorium caespitum.

  From the order of the louse, for example, Pediculus humanus capitis, Pediculus humanus corpolis, Penfigus sp., Philoera busturrix

  From the order of the order of the bugs, for example, Chimex hemipterus, Chimex rectularius, Rhodinus prolixus, Triatoma infestans.

  In the field of household insecticides, the active compound can be used alone or with another suitable active compound (eg phosphate ester, carbamate, pyrethroid, neonicotinoid, growth regulator, or other known Active compounds from the class of pesticides, etc.).

  The active compounds may be aerosols, non-pressurized spray products (eg pump sprays and spray sprays), automatic atomization systems, nebulizers, foams, gels, evaporator tablets with cellulose or polymer evaporator tablets. -Tater products, liquid evaporators, gel and membrane evaporators, propeller driven evaporators, energy-free or passive evaporation systems, insect papers, insect bags Used in bags and spreading gels or bait stations, as granules or powders, in baits for spreading or bait stations.

  The active compound / active compound combinations according to the invention can also be used as dead leaves, desiccants, haul killers and in particular as weed killers. Weeds are understood in a broad sense to mean all plants that grow in undesirable places. Whether the substances according to the invention act as non-selective or selective herbicides basically depends on the application rate.

  The active compound / active compound combination according to the invention can be used, for example, in the following plants:

  Genus of dicotyledonous weeds: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Hamaakagi, Atriplex Genus (Belis), Sendangusa (Bidens), Nazuna (Capsella), Calamus, Cardigan, Cassaria, Centaurea, Chenopodium, Cirsium, Cirrus Genus (Convolvulus), datura (Datura), genus genus (Desmodium), genus Emex (Emex), genus Ezoshiroshiro (Ery Immum), Euphorbia, Galeopsis, Galinosa, Galium, Hibiscus, Ipomoea, Om, L , Lepidium, Lindernia, Matricaria, Mentha, Mencurialis, Mulgo, Patricae, Myosivis , Pharbitis, Plantago, Polygonum, Portarum (Port) laca), buttercup genus (Ranunculus), radish genus (Raphanus), red genus (Roripppa), genus genus (Rotala), genus genus (Rumex), genus (Salsola), genus (Seneci), , Genus Sida, Sinapis, Solanum, Sonchus, Sphenocrea, Stellaria, Taraxacum, Gumba sp. Rhododendron (Trifolium), Nettle (Urtica), Staghorn (Veronica), Violet (Viola), Onamomi (Xan) thium).

  Genus of dicotyledonous crops: arachis, chard (Beta), Brassica, cucumber, cucurbita, helianthus, carrot (Daucus), soybean Genus (Glycine), cotton genus (Gossypium), sweet potato genus (Ipomoea), genus Akinogeshi (Lactuca), genus Linma, tomato genus (Lycopersicon), genus Tobacco (Nicotiana), common bean genus (Phaseol) Pisum), Solanum, Vicia.

  The genus of monocotyledonous weeds: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, B-Ara, B , Genus Bromus, genus Cenchurus, genus Commelina, cynodon, cyperus, genus Dactylite, genus D. , Genus Eleocharis, genus Eleusine, genus Egrostis, genus Narcobier ( riochloa, genus Festuca, Fembristilis, Heteranthera, Imperata, Ichaeumon, Leptochloi, Leptochloi , Millet genus (Panicum), genus Paspalum, genus Phallaris, genus pearl moth (Phlum), genus Strawberry (Poa), genus Lotboella (Sottitalia), genus Sagittaria (c) ), Enocologosa (Setaria), Sorghum.

  The genus of monocotyledonous crops: Allium, Ananas, Asparagus, Asenagus, Avena, Barley, Oryza, Panicum, Sugarcane (Saccharum), Rye (Secale), Sorghum, Triticale, Triticum, Corn (Zea).

  However, the use of the active compound / active compound combination according to the invention is not limited to these genera in any way and extends to other plants as well.

  Depending on the concentration, the active compound / active compound combination according to the invention is suitable, for example, for non-selective weed control in industrial areas and railways and on roads and places with or without trees. Similarly, the active compounds according to the invention are perennial crops (eg forests, ornamental tree plantations, orchards, vineyards, citrus gardens, nut gardens, banana gardens, coffee gardens, tea gardens, rubber gardens, oil palm gardens, cacao gardens. , Soft fruit plantations, and hop fields), lawns (lawns), turf, and pastures, and selective control of annual crop weeds.

  The compounds of formula (I) / active compound combinations according to the invention have a strong herbicidal activity and a broad spectrum of activity when used in soil and on terrestrial plant parts. To some extent, these combinations are also suitable for selective control of monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops, both before and after emergence.

  The active compound / active compound combinations according to the invention can also be used to control harmful animals and fungal or bacterial plant diseases at a certain concentration or application rate. If appropriate, they can also be used as intermediates or precursors for the synthesis of other active compounds.

  The active compound / active compound combination is a normal formulation (solution, emulsion, wettable powder, suspension, powder, dusting agent, paste, soluble powder, granule, suspension emulsion concentrate). , Natural and synthetic materials impregnated with active compounds, and very fine capsules in polymeric materials).

  Such formulations are prepared in a known manner, for example with the active compound as a bulking agent (which is a liquid solvent and / or a solid carrier) and optionally a surfactant (emulsifier and / or dispersant and / or foam former). )) And mixed.

  When the extender used is water, for example, an organic solvent can be used as an auxiliary solvent. In essence, suitable liquid solvents are aromatics (such as xylene, toluene, or alkylnaphthalene), chlorinated aromatic and chlorinated aliphatic hydrocarbons (such as chlorobenzene, chloroethylene, or methylene chloride), aliphatic hydrocarbons (such as Cyclohexane or paraffin, such as petroleum fractions, mineral oils and vegetable oils), alcohols (such as butanol or glycol) and their ethers and esters, ketones (such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone), strong polar solvents (dimethylformamide) And dimethyl sulfoxide), and water.

  Suitable solid carriers include, for example, ammonium salts and ground natural minerals (such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite, or diatomaceous earth), and ground synthetic minerals (highly dispersible silica, Solid supports suitable for granules include, for example, natural rocks (such as calcite, marble, pumice, ganolite, and dolomite) that have been ground and separated, and inorganic and organic coarse powders. And granules of organic materials (such as sawdust, coconut shells, corn cob, and tobacco petiole); suitable emulsifiers and / or foam formers are, for example, nonionic and anionic emulsifiers (Polyoxyethylene fatty acid ester, polyoxyethylene aliphatic alcohol ether, for example Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, and aryl sulfonate), and there protein hydrolysates; suitable dispersants are: for example lignosulfite waste liquors and methylcellulose.

  Tackifiers such as carboxymethylcellulose, and natural and synthetic polymers in the form of powders, granules, or latex (such as gum arabic, polyvinyl alcohol, and polyvinyl acetate), as well as natural phospholipids (such as cephalin and lecithin) , As well as synthetic phospholipids and the like can be used in the formulation. Other possible additives are mineral and vegetable oils.

  Colorants such as inorganic pigments (eg, iron oxide, titanium oxide, and Prussian blue), and organic dyes (such as alizarin dyes, azo dyes, and metal phthalocyanine dyes), and micronutrients (iron salts, manganese salts, Boron salts, copper salts, cobalt salts, molybdenum salts, and zinc salts, etc.) can also be used.

  The formulations generally comprise between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.

  The active compound / active compound combination according to the invention can be used as it is or in these formulations as a mixture with known herbicides and / or with substances that improve crop tolerance ("toxication"). It can also be used for purposes and can be pre-mixed or tank mixed. Mixtures with herbicidal products containing one or more known herbicides and safeners are therefore possible.

Suitable herbicides for the mixture are known herbicides, for example:
Acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim (-sodium), ametrine, amicarbazone, amikacarbamide Amidosulfuron, aminopyralide, anilofos, asuram, atrazine, azafenidin, azizulfuron, eflusulfina (b) zolin (-ethyl), benfuresate, bensulfuron (-methyl), bentazone, bencarbazone, benzfendizone, benzobicyclon (benzobicone) (Benzofenap), benzoylprop (-ethyl), bialaphos, bifenox, bispiribac (-sodium), bromobutoxyl (bromophenoxyl), bromophenoxyl (bromophenoxyl) ), Butafena Butafenacil (-allyl), butroxydim, butyrate, cafenstrol, caroxydim, carbetamide, carfentrazone (carfentrazone) ), Chloromethoxyphen, chloramben, chloridazon, chlorimuron (-ethyl), chlornitrofen, chlorsulfuron, chlortoluurone, chlortoluurone -Ethyl), thin Methyline, cynosulfuron, cleoxidim, cletodim, clodinafop (-propargyl), clomazone, clomeprod ) (-Methyl), chloranthram (-methyl), cumyluron, cyananadine, sibutryne, cycloate, cyclosulfamuron, cycloxydimoxy lofop (-butyl), 2,4-D, 2,4-DB, desmedifam, diallate, dicamba, dichlorprop (-P), diclohop (-methyl) , Dicloslam, diethatyl (-ethyl), diphenzocot, diflufenican, diflufenzopyr, dimefuron, dimethachlor, dimethachlor, dimethachlor, dimethachlor (Dimethenamid), dimexiflam, dinitramine ( initramine, diphenamide, diquat, dithiopyr, diuron, diuron, epropodan, EPTC, esprocarb, etalfluralin ethamesulfuron (-methyl), ethofumesate, ethoxyphene, ethoxysulfuron, ethozanid, phenoxaprop (z), p flampr op) (-isopropyl, -isopropyl-L, -methyl), flazasulfuron, florasulfam, fluazifop (-P-butyl), fluazolate, flucarbazone (flucarbazone) -Sodium), flufenacet, flumeturam, flumiclorac (-pentyl), flumioxazin, flumipropyn, flumeturone, flueturon, flueturon Fen (fluorogl cofen) (-ethyl), flupoxam, flupropacil, flurpyrsulfuron (-methyl, -sodium), flurenol (-butyl), fluridone (fluroxypy), fluroxypy -Butoxypropyl, -meptyl), flurprimidol, flurtamone, fluthiacet (-methyl), fluthiamide, fomesaful, folamulone, folsamul -Glufosinate (-ammonium , Glyphosate (-isopropylammonium), halosafen, haloxyhop (-ethoxyethyl, -P-methyl), hexazinone, HOK-201, imazametathenz (-methyl), imazametapyr imazamethapyr), imazamox, imaxyur, imazapyr, imazapyr, imazapyr, imazapyr ), Isopropaline (isopr) opalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifole, lactofen (Linuron), MCPA, mecoprop, mefenacet, mesosulfurone, mesotrione, metamihop, metamithrone, metazamethrazol uron), methbenzuron, methobromuron, (α-) metolachlor, methoslam, methoxuron, metribuzon, methululuron, metululuron, metsulfuron molinate, monolinuron, naproanilide, napropamide, neburon, nicosulfuron, norflurazon, olbencarb, olbencarb on), oryzalin, oxadiaargyl, oxadiazon, oxasulfuron, oxadichromefone, oxyfluorfen, p-quat (p) Pendimethalin, pendralin, penoxulam, pentoxazone, phenmedipham, picolinafen, pinoxenphos, pinoxen Pretilachlor, primisulfuron (-methyl), profluazol, promethrin, propachlor, propanporo, propaporo, propaporo. propoxycarbazone (-sodium), propyzamide, prosulfocarb, prosulfuron, pyraflufen (-ethyl), pyrasulfotopyrafozole gyl), pyrazolate, pyrazosulfuron (-ethyl), pyrazoxifene, pyribenzoxim, pyributicarb, pyridol, pyridol, pyridol, pyridol. pyriminobac (-methyl), pyrimisulfan, pyrithiobac (-sodium), pyroxslam, piroxasulfone (quinoxlac), quinchloracin noclamine), quizalofop (-P-ethyl, -P-tefuryl), rimsulfuron, cetoxydim, simazine, simulon, simetrion Fentrazone, sulfometuron (-methyl), sulfate, sulfosulfuron, tebutam, tebuthiuron, tembotrion, tembotrion ), Terbuthylazine (terbu thylazine, terbutryn, tenylchlor, thiafluamide, thiazopyr, thidiazimin, thiazimin,
thiencarbazone-methyl), thifensulfuron (-methyl), thiobencarb, thiocarbazil, topramzone, traltriatritol, tralkoxytrilto (Tribenuron) (-methyl), triclopyr, tridiphane, trifluralin, trifluoxysulfuron, triflusulfuron (-methyl), triflusulfuron (-methyl) (Tritosulfuron), and

  Mixtures with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients, and soil conditioners are also possible.

  The active compound or compound combination is left as is, in the form of this formulation, or in the form of use prepared from it (by ready-to-use solutions, suspensions, emulsions, powders, pastes, granules, etc.) by further dilution Can be used. The active compounds or compound combinations are used in the usual manner, for example by pouring, spraying, spraying and spreading.

  The active compounds or compound combinations according to the invention can be used both before and after emergence. The active compound or compound combination can also be incorporated into the soil before planting.

  The application rate of the active compound can vary within a substantial range. In essence, the spread rate depends on the nature of the desired effect. In general, the application rate is between 1 g and 10 kg of active compound per hectare of soil area, preferably between 5 g and 5 kg per ha.

  The advantageous effect of compatibility of the active compound combinations according to the invention with crops is particularly pronounced at certain concentration ratios. However, the weight ratio of active compound in the compound combination can vary within a relatively wide range. In general, 0.001 to 1000 parts by weight of one salt of the crop compatibility improving compound (antidote / toxicant) described in (b ′) above per part by weight of the active compound of formula (I) , Preferably 0.01 to 100 parts by weight, particularly preferably 0.05 to 20 parts by weight.

  The active compound combinations according to the invention are generally used in the form of final formulations. However, the active compounds contained in the active compound combinations can also be mixed at the time of use as individual formulations, ie used in the form of tank mixing.

  For certain use cases, in particular postemergence use, as additional additives to the formulation, the plant-tolerant mineral oil or vegetable oil (eg the commercial formulation “Rako Binol”), or ammonium salts (eg ammonium sulfate) Or ammonium thiocyanate, etc.).

  The novel active compound combination is used as it is, in the form of this formulation or in the form of use prepared from it, by further dilution (such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules) Can be done. The use is in the usual manner, for example by pouring, spraying, spraying, dusting or scattering.

  The application rate of the active compound combinations according to the invention can vary within a certain range. The amount of application depends inter alia on the weather and soil factors. In general, the application rate is between 0.001 g and 5 kg per ha, preferably between 0.005 g and 2 kg per ha, particularly preferably between 0.01 and 0.5 kg per ha.

  The active compound combinations according to the invention can be used before and after the emergence of plants, i.e. in the preemergence and postemergence methods.

  Depending on this property, the safener to be used according to the invention can be used to pre-treat the seeds of the crop (seed dressing) and can be introduced between the seed pods before sowing, or It can be used before or after the emergence of the plant, before the herbicide, separately or together with the herbicide.

  The fungicides are crop protection, Plasmodiophormycetes, Omycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Ascomycetes, Ascomycetes It can be used to control Deuteromycetes.

  The fungicides are used for crop protection, Pseudomonadaceae, Rhizobaceae, Enterobacteriaceae, Corynebacteriaceae, and Streptomyces acetaceae. be able to.

  Some of the pathogens causing fungal and bacterial diseases classified in the above genus names can be mentioned as examples, not as limitations.

Xanthomonas species, such as Xanthomonas campestris pv. Oryzae;
Pseudomonas species, such as Pseudomonas syringae pv. Lacrymans;
Erwinia species, such as Erwinia amylovora;
Pythium species, such as Pythium ultimum;
Phytophthora species, such as Phytophthora infestans;
Pseudoperonospora species, such as Pseudoperonospora humuli or Pseudoperosporum cubensis;
Plasmopara species, such as Plasmopara viticola;
Bremia species, such as Bremia lactucae;
Peronospora species, such as Peronospora pisi or P. aeruginosa. Brush frog (P. brassicae) and the like;
Erysiphe species, such as Erysiphe graminis;
Sphaerotheca species, such as Sphaerotheca friginea;
Podosphaera species, such as Podosphaera leucotrica;
Venturia species, such as Venturia inequalis;
Pyrenophora species, such as Pyrenophora teres or P. aeruginosa. Graminea (P. graminea)
(Conidia form: Drechslera, synonym: Helmintosporium) and the like;
Cochliobolus species, for example, Cochliobols sativus
(Conidia form: Drexerrera, synonymous: Hermint sporium) etc .;
Uromyces species, such as Uromyces appendiculatus;
Puccinia species, such as Puccinia recondita;
Sclerotinia species such as, for example, Sclerotinia sclerotiorum;
Tilletia species, such as Tilletia caries, etc .;
Ustylago species, such as Ustyago nuda or Ustylaga avenae;
Pericularia species, such as Pericularia sasakii;
Pyricularia species, such as Pyricularia oryzae;
Fusarium species, such as Fusarium culmorum;
Botrytis species, such as Botrytis cinerea, etc .;
Septoria species, such as Septoria nodolum;
Leptosphaeria species, such as Leptosphaeria nodorum;
Cercospora species, such as Cercospora canescens;
Alternaria species such as Alternaria brassicae; and Pseudocercosporella species such as Pseudocercosporellaherp.

  The active compounds according to the invention also have a very good forcing action in plants. Thus, the active compounds according to the invention can be used to mobilize the defenses of plants against attack by unwanted microorganisms.

  In the present text, plant fortification (resistance-inducing) substances are those of the plant so that when the treated plant is subsequently inoculated with undesirable microorganisms, it exhibits substantial resistance to such microorganisms. It should be understood to mean such substances capable of stimulating the defense system.

  In the present invention, undesirable microorganisms are to be understood as meaning phytopathogenic fungi, bacteria and viruses. The substances according to the invention can therefore be used to protect plants from attack by the described pathogens for a certain period after treatment. The period during which protection is provided generally ranges from 1 to 10 days, preferably from 1 to 7 days after treatment of the plant with the active compound.

  The fact that plants are sufficiently tolerant to active compounds at concentrations necessary to control plant diseases allows for the treatment of above-ground parts of plants, propagation stock and seeds, and soil. .

  The active compounds according to the invention are also suitable for increasing the crop yield. The active compounds according to the invention also show a reduced toxicity and the plants have a sufficient tolerance.

  At certain concentrations and application rates, the active compounds according to the invention can also be used as herbicides, if appropriate, to affect plant growth and to control harmful animals. If appropriate, the active compounds according to the invention can also be used as intermediates and precursors for the synthesis of further active compounds.

  In the protection of materials, the substances according to the invention can be used to protect industrial materials from infection and destruction by unwanted microorganisms.

  In the text, industrial material is understood to mean a lifeless material prepared for industrial use. For example, industrial materials intended to protect against microbial changes or destruction with the active compounds according to the invention include adhesives, sizes, paper and board, cloth, leather, wood, plant and plastic articles, cooling lubricants, and microorganisms. There may be other materials that can be infected or destroyed by. Some parts of the manufacturing plant (eg, cooling channels) that may fail due to microbial growth can also be included within the scope of the material to be protected. The industrial materials that can be mentioned within the scope of the invention are preferably adhesives, sizes, paper and board, leather, wood, plants, cooling lubricants and heat exchange fluids, particularly preferably wood.

  Mention may be made, for example, of bacteria, fungi, yeasts, algae, and myxomycetes, which can be cited as microorganisms capable of degrading or altering industrial materials. The active compounds according to the invention preferably act against fungi, in particular fungi, wood depigmenting fungi, and wood-degrading fungi (Basidiomycetes), as well as against myxomycetes and algae.

The following genera of microorganisms can be mentioned as examples.
Alternaria, for example, Alternaria tenuis,
Aspergillus, for example Aspergillus niger,
Genus Chaetomium, for example, Chaetomium globosum,
Coniophora, such as Coniophora puteana,
Lentinus, such as Lentinus tigrinus,
Penicillium, such as Penicillium glaucum,
Genus Polyporus, for example Polyporus versicolor,
Aureobasidium, such as Aureobasidium pullulans,
Genus Sclerophoma, for example, Sclerophoma pithiophila,
Trichoderma, for example, Trichoderma viride,
Escherichia, such as Escherichia coli,
Pseudomonas, such as Pseudomonas aeruginosa,
Staphylococcus, for example Staphylococcus aureus.

  Depending on the specific physical and / or chemical properties, the active compound can be used in conventional formulations (solutions, emulsions, suspensions, powders, foams, pastes, granules, and seed polymer substances). And microencapsulated in coating compositions, and ULV cooled and thermal atomized formulations, etc.).

  The formulations are known in the manner that, for example, the active compound is mixed with a bulking agent (which is a liquid solvent, a compressed liquefied gas and / or a solid carrier) and optionally a surfactant (emulsifier and / or dispersant, and And / or a foam-forming agent). When the extender used is water, for example, an organic solvent can be used as an auxiliary solvent. In essence, suitable liquid solvents are aromatic compounds (such as xylene, toluene, or alkylnaphthalene), chlorinated aromatic and chlorinated aliphatic hydrocarbons (such as chlorobenzene, chloroethylene, or methylene chloride), aliphatic hydrocarbons (Cyclohexane or paraffins such as petroleum fractions), alcohols (such as butanol or glycol) and their ethers and esters, ketones (such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone), strong polar solvents (dimethylformamide and Dimethyl sulfoxide, etc.) or water. A liquefied gas extender or carrier should be understood to mean a liquid that is gaseous at standard temperature and atmospheric pressure (eg, aerosol propellants such as halogenated hydrocarbons or butane, propane, nitrogen and carbon dioxide). It is. Suitable solid supports include, for example, ground natural minerals (such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite, or diatomaceous earth), and ground synthetic minerals (such as highly disperse silica, alumina, and silicates). It is. Suitable solid carriers for granules include, for example, natural granulated rocks (such as calcite, marble, pumice, gizzard, and dolomite), or synthetic granules composed of inorganic and organic coarse powders, and Granules of organic materials such as sawdust, coconut shells, corn cob, and tobacco petiole. Suitable emulsifiers and / or foam formers are, for example, nonionic and anionic emulsifiers (polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers such as alkylaryl polyglycol ethers, alkylsulfonates, alkylsulfonates). Ferment, aryl sulfonate, etc.) or protein hydrolyzate. Suitable dispersing agents are, for example, lignosulfite waste liquor and methylcellulose.

  Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latex (such as gum arabic, polyvinyl alcohol and polyvinyl acetate) or natural phospholipids (such as cephalin and lecithin) , And synthetic phospholipids can be used in the formulation. Other possible additives are mineral and vegetable oils.

  Colorants such as inorganic pigments (iron oxide, titanium oxide and Prussian blue), organic dyes (alizarin dyes, azo dyes and metal phthalocyanine dyes), and micronutrients (iron salts, manganese salts, boron salts, copper) Salts, cobalt salts, molybdenum salts, and zinc salts) can be used.

  The formulations generally comprise between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.

  The active compounds according to the invention can be used as such or in this formulation, for example in order to broaden the spectrum of activity or to prevent the acquisition of resistance, known fungicides, fungicides, acaricides, nematicides, or It can also be used in a mixture with an insecticide. In many cases, a synergistic effect is obtained, ie the activity of the mixture is higher than the activity of the individual components.

  Examples of suitable mixing components are the compounds described above (fungicides, fungicides, insecticides, acaricides, nematicides).

  Mixtures with other known active compounds (such as herbicides) or with fertilizers and growth regulators are also possible.

  The compounds of formula (I) according to the invention also have very good antifungal activity. The compounds of formula (I) according to the invention exhibit a very broad spectrum of antifungal activity, in particular dermatophytes and yeasts, molds and diphasic fungi (eg Candida albicans, Candida -Candida species such as Gravata (Candida glabrata), as well as Epidermophyton floccosum, Aspergillus species (Aspergillus niger and Aspergillus fumigaton, Aspergillus phytograph) ) Species (Trichophyton mentagrophytes) s), etc.), micro Suporon (Microsporon) species (micro Suporon canis (Microsporon canis) and O - has on Dounii (Audouinii), etc.). The enumeration of these fungi does not limit the range of the mold spectrum in any way and is merely exemplary.

  The active compound can be used as it is as a ready-to-use solution, suspension, wettable powder, paste, soluble powder, powder, granule, etc. in this formulation or the usage form prepared therefrom. it can. The use is carried out in the usual manner, for example by pouring, spraying, spraying, broadcasting, dusting, foaming and spreading. It is further possible to use the active compound in an ultratrace manner or to inject the active compound formulation or the active compound itself into the soil. It is also possible to treat plant seeds.

  When using the active compounds according to the invention as fungicides, the application rate can vary within a relatively wide range, depending on the type of application. For the treatment of plant parts, the active compound application rate is generally between 0.1 and 10,000 g / ha, preferably between 10 and 1000 g / ha. For seed modification, the active compound application rate is generally between 0.001 and 50 g per kg seed, preferably between 0.01 and 10 g per kg seed. For soil treatment, the active compound application rate is generally between 0.1 and 10,000 g / ha, preferably between 1 and 5000 g / ha.

  The term “active compound” includes a formulated composition containing the active compound combination described, as well as ammonium and / or phosphonium salts and, if appropriate, penetrants.

  The preparation and use of the active compounds according to the invention is illustrated by the following examples.

(Example)
Preparation Example (Example I-1-a-1)

  First, potassium tert-butoxide is added to 2 ml of dimethylacetamide and heated to 100 ° C. At this temperature, 3 ml of the dimethylacetamide solution according to Example II-1 are added in 10 portions over 1 hour. The mixture is stirred at 100 ° C. for 2 hours, 20 ml of water are added and the pH is adjusted to 1 with concentrated hydrochloric acid. The mixture is then concentrated into 50 ml of dichloromethane, dried over sodium sulfate and concentrated. Purification by column chromatography (gradient (n-heptane / ethyl acetate 4: 1 to ethyl acetate) gives 80 mg of the expected product, melting point: 209-217 ° C. (yield: 42% of theory).

  The following compounds of formula (I-1-a) are obtained analogously to Example (I-1-a-1) according to the general description of the preparation.

  (Example I-1-b-1)

  First, 0.18 g of the compound of Example I-1-a-6 was added to 8 ml of ethyl acetate, 0.1 ml of triethylamine and 1.5 mg of 4-N, N′-dimethylaminopyridine were added, and the mixture was heated to 60 ° C. Heat to. A solution of 0.07 g of isobutyryl chloride in 2 ml of ethyl acetate is added in 7 portions over 60 minutes and the mixture is stirred at 60 ° C. for 6 hours. The mixture is allowed to stand overnight, then half-concentrated sodium chloride solution is added to separate the organic phase and silica gel column chromatography (gradient is EtOAc / n-heptane 1: 9 to ethyl acetate / n-heptane). To 100: 0). This gives 85 mg of a colorless solid (38% of the theoretical yield). Melting point 126-134 ° C

  The following compounds of formula (I-1-b) are obtained analogously to Example (I-1-b-1) according to the general description of the preparation.

  (Example I-1-c-1)

0.077 g (0.219 mmol) from Example I-1-a-5 is dissolved in 3 ml dichloromethane, 0.04 ml (1.2 eq) triethylamine is added and the mixture is stirred at room temperature for 10 minutes. Then 0.02 ml (1.1 eq) of ethyl chloroformate is added and the mixture is stirred overnight at room temperature. After extraction with 4% strength Na ₂ CO ₃ solution, the organic phase is dried, concentrated and purified by column chromatography on silica gel (gradient n-heptane / ethyl acetate 9: 1 to ethyl acetate). This gives 44 mg of product as a solidified glass (yield: 47% of theory).
¹ H-NMR (400 MHz, CDCl ₃ ) δ = 3.32 (s, 3H, CH—OCH ₃ ), 3.76 (s, 3H, Ar—OCH ₃ ), 4.05 (q, 2H, OCH ₂ ) Ppm.

  Example (I-1-c-2) is obtained in the same manner as Example (I-1-c-1).

^１Ｈ−ＮＭＲ（４００ＭＨｚ，ＣＤＣｌ_３）δ＝３．３２（ｓ，３Ｈ，ＣＨ−ＯＣＨ_３）、２．５８（ｍ，２Ｈ，Ａｒ−ＣＨ_２）、４．０７（ｑ，２Ｈ，ＯＣＨ_２）ｐｐｍ。

¹ H-NMR (400 MHz, CDCl ₃ ) δ = 3.32 (s, 3H, CH—OCH ₃ ), 2.58 (m, 2H, Ar—CH ₂ ), 4.07 (q, 2H, OCH ₂₎ ) Ppm.

  According to the general description of the preparation, a compound of the following formula (I-1-c) is obtained in the same manner as in Examples (I-1-c-1) and (I-1-c-2).

  (Example I-1-d-1)

0.156 g of the compound according to Example I-1-a-21 is dissolved in 10 ml of dichloromethane and 0.06 ml of triethylamine is added. To this solution is added 0.032 ml of methanesulfonyl chloride and the mixture is stirred at room temperature for 20 hours. After stirring the mixture with 5 ml of 5% strength sodium bicarbonate solution for 0.5 h, the organic phase is separated off, dried over sodium sulfate and concentrated using a rotary evaporator, and the resulting residue is subjected to column chromatography (gradient n -Heptane + ethyl acetate 9: 1 to ethyl acetate).
Yield: 0.14 g (76% of theory).
¹ H-NMR (CDCl ₃ , 400 MHz): δ = 4.16 ppm (m, 1H, CH—O), 2.62 ppm (s, 3H, SO ₂ CH ₃ ), 2.32 ppm, (s, 3H, Ar _{-CH 3), 1.03ppm (m,} 1H, CH- cyclopropyl).

  (Example I-1-f-1)

0.1 g of the compound according to Example I-1-a-21 is dissolved in 7 ml of anhydrous methanol and 0.045 ml of 30% strength sodium methoxide solution is added. After 2 hours, the solution is concentrated using a rotary evaporator, and further, 5 ml each of anhydrous methanol is added twice, and the mixture is concentrated using a rotary evaporator and dried under high vacuum.
Yield: 0.095 g (90% of theory).
¹ H-NMR (d6-DMSO, 400 MHz): δ = 5.01 ppm (m, 1H, CH—O), 2.21 ppm (s, 3H, Ar—CH ₃ ), 0.45 and 0.16 ppm (respectively m, 2H, CH-cyclopropyl).

  (Example I-1-g-1)

0.158 g of the compound according to Example I-1-a-21 is dissolved in 10 ml of chloroform and 0.08 ml of diisopropylethylamine and 2 mg of DMAP are added. 0.048 ml of morpholine-N-carbonyl chloride is added and the solution is stirred at room temperature for 20 hours. The mixture is then stirred with 5 ml of 5% strength sodium bicarbonate solution for 0.5 hour, the organic phase is separated off, dried over sodium sulfate, concentrated using a rotary evaporator and the resulting residue is subjected to column chromatography ( The gradient is purified with n-heptane + ethyl acetate 9: 1 to ethyl acetate).
Yield: 0.14 g (63% of theory).
¹ H-NMR (CDCl ₃ , 400 MHz): δ = 4.14 ppm (m, 1H, CH—O), 36-31 ppm (multiple multiplets, 10H, CH ₂ O and CH ₂ N signals), 2.32 ppm _{(s, 3H, Ar-CH} 3).

  Example II-1

  0.41 g (1.23 mmol) from Example II-10 is dissolved in 15 ml dichloromethane. 0.29 g (1.1 eq) of 1,8-bisdimethylaminonaphthalene and 0.20 g (1.1 eq) of trimethyloxonium tetrafluoroborate are added and the mixture is stirred at room temperature. Then, after each 4 hours, once each 0.3 equivalent of trimethyloxonium tetrafluoroborate and 1,8-bismethylaminonaphthalene are added and the mixture is again stirred overnight. Then 20 ml of 5% strength citric acid are added, the mixture is stirred for 45 minutes and the organic phase is separated off, dried over sodium sulphate and chromatographed on silica gel (gradient is n-heptane / ethyl acetate 4: 1 to ethyl acetate). To be purified.

This gives 0.27 g of product (63% of theoretical yield).
¹ H-NMR (400 MHz, CDCl ₃ ) δ = 4.16 (q, 2H, CH—OCH ₂ ), 3.93 (m, 1H, CH—OCH ₃ ), 3.56 (s, 2H, CH _{2 -Ar), 3.26 (s, 3H} , OCH 3) ppm.

Heat 1.05 g (5.89 mmol) of mesitylene acetic acid, 6 ml of thionyl chloride and 2 drops of N, N-dimethylformamide to reflux. After the evolution of gas has ceased, the mixture is concentrated and placed in 20 ml of dichloromethane (solution 1). 1.25 g (2.1 eq) of triethylamine is added to a solution of ethyl 3-hydroxy-1-aminocyclopentanecarboxylate (5.89 mmol) and the mixture is stirred for 10 minutes. Solution 1 is added dropwise at room temperature over 20 minutes. The mixture is left stirring overnight at room temperature. The mixture is washed with 15 ml of water, the organic phase is dried over sodium sulphate and purified by column chromatography on silica gel (gradient is ethyl acetate / n-heptane 0: 100 to 100: 0). This gives 0.95 g of cis isomer (yield: 48% of the theoretical amount) and 0.43 g of trans isomer (yield: 22% of the theoretical amount).
trans isomer Example II-10
¹ H-NMR (400 MHz, CDCl ₃ ) δ = 4.38 (m, 1H, CHOH), 3.53 (s, 2H, Ar—CH ₂ ) ppm
cis isomer Example II-9
¹ H-NMR (400 MHz, CDCl ₃ ) δ = 4.21 ppm (m, 1H, CHOH), 3.60 (s, 2H, Ar—CH ₂ ) ppm
(Example II-34)

First, 1.87 g of mesityl acetic acid and 6.25 g of thionyl chloride are added and 2 drops of dimethylformamide are added. The mixture is then heated until gas evolution ceases, concentrated and dissolved in 25 ml of dichloromethane (Solution 1). Compound 2.49 of Example (XIV-2) is dissolved in 25 ml of dichloromethane, 3.06 ml of triethylamine is added, then solution 1 is added dropwise over 30 minutes and the mixture is stirred at room temperature overnight. Semi-concentrated sodium chloride solution is added, the phases are separated, the organic phase is concentrated, dried over sodium sulfate, and column chromatography (gradient is ethyl acetate / heptane 5:95 to 70:30 ethyl acetate). Purify.
Yield: 1.91 g (38% of theory)
¹ H-NMR (400 MHz, CDCl ₃ ) δ = 6.89 ppm (d, 1H, Ar—H), 3.35 ppm (d, 3H, OCH ₃ ), 1.24 ppm (t, 3H, CH ₃ —CH ₂₎ O).

  The following compounds of formula (II) are obtained analogously to Examples (II-1), (II-9), (II-10) and (II-34) according to the general description of the preparation.

エチル３−ヒドロキシ−１−アミノ−１−シクロペンタンカルボキシレート

Ethyl 3-hydroxy-1-amino-1-cyclopentanecarboxylate

ＷＯ０２／４６１２８と同様
ナトリウムヒドリド９．１８８ｇ（６０％、２．２当量）を無水テトラヒドロフラン４００ｍｌに懸濁させ、エチルＮ−（ジフェニルメチレングリシナート２７．９１４ｇ（１当量）をテトラヒドロフラン１００ｍｌに溶解させたものを３０分かけて滴下する。混合物を３０分間撹拌し、次いでジブロミドＡ^＊（テトラヒドロフラン１００ｍｌに溶解）を３０分かけて滴下する。混合物を、最初に還流下４時間撹拌し、次いで室温で一晩撹拌する。

Similar to WO 02/46128, 9.188 g (60%, 2.2 equivalents) of sodium hydride was suspended in 400 ml of anhydrous tetrahydrofuran, and 27.914 g (1 equivalent) of ethyl N- (diphenylmethylene glycinate) was dissolved in 100 ml of tetrahydrofuran. The mixture is stirred for 30 minutes, and then dibromide A ^* (dissolved in 100 ml of tetrahydrofuran) is added dropwise over 30 minutes. Stir overnight.

Then 0.6 l of water and 1.2 l of acetic acid are added and the solution is left stirring at an internal temperature of 55 ° C. for 8 hours. The mixture is left overnight, then concentrated, 0.6 l of water is added, the pH is adjusted to pH = 7 with sodium bicarbonate, and the mixture is concentrated again. Three times to each residue obtained in this manner 0.4 l of dichloromethane are added and the organic phases are combined and dried over sodium sulfate. This gives 9.8 g of product as a viscous oil. (54.2% of theoretical yield)
¹ H-NMR (CDCl ₃ , 400 MHz): δ = 4.20 (m, 2H, OCH ₂ ), 4.35 and 4.50 (each m, together 1 H, CH—OH) ppm.
^* Dibromide A = 1,4-dibromo-2- (2′-tetrahydropyranyl) oxybutaneethyl 3-methoxy-1-amino-1-cyclopentanecarboxylate (XIV-1)

Ａ．Ｂｏｅｒｎｅｒ等、Ｃｈｅｍ．Ｂｅｒ．１２８，７６７（１９９５）
Ｍａ，Ｄａｗｅｉ等、Ｔｅｔｒａｈｅｄｒｏｎ
Ａｓｙｍｍｅｔｒｙ ８，８２５（１９９７）と同様
ナトリウムヒドリド０．６３７ｇ（６０％、２．２当量）を無水テトラヒドロフラン２０ｍｌに懸濁し、エチルＮ−（ジフェニルメチレングリシナート１．９３５ｇ（１当量）（テトラヒドロフラン１００ｍｌに溶解）を、３０分かけて滴下する。混合物を３０分間撹拌し、ビスメシレートＡ^＊（テトラヒドロフラン１０ｍｌに溶解）を３０分かけて加える。混合物を、最初に還流下４時間撹拌し、次いで室温で一晩撹拌する。

A. Boerner et al., Chem. Ber. 128,767 (1995)
Ma, Dawei et al., Tetrahedron
Similar to Asymmetry 8,825 (1997) Sodium hydride 0.637 g (60%, 2.2 eq.) Was suspended in 20 ml of anhydrous tetrahydrofuran and ethyl N- (diphenylmethylene glycinate 1.935 g (1 eq.) (100 ml of tetrahydrofuran in 100 ml). Dissolve) is added dropwise over 30 minutes, the mixture is stirred for 30 minutes, and bismesylate A ^* (dissolved in 10 ml of tetrahydrofuran) is added over 30 minutes. Stir overnight.

Then 40 ml of water and 80 ml of acetic acid are added to the solution and the mixture is stirred at an internal temperature of 55 ° C. for 8 hours. The mixture is left overnight, then concentrated, 50 ml of water are added, the pH is adjusted to pH = 7 with sodium bicarbonate and the mixture is concentrated again. Three times to the residue obtained, 0.1 l each of dichloromethane is added and the organic phases are combined and dried over sodium sulfate. This gives 0.75 g of product as a viscous oil. (52.7% of theoretical yield).
^* Bismesylate A = 2-methoxy-1,4-butanediol-bismesylate

  The following compounds of formula (XIV) are obtained analogously to Example (XIV-1) according to the general description of the preparation.

Example of use

Fedon test (PHAECO spray treatment)
Solvent: 78 parts by weight of acetone 1.5 parts by weight of dimethylformamide Emulsifier: 0.5 parts by weight of alkylaryl polyglycol ether In order to produce a suitable preparation of the active compound, 1 part by weight of active compound is added in the amount of solvent described. And mixed with emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.

  A Chinese cabbage (Blassica pekinensis) disc is sprayed with the active compound preparation of the desired concentration, dried and then loaded with larvae of Master dovitol (Fedon cocleariae).

  After the desired period, the effect is determined in%. 100% means that all the beetle larvae have been killed; 0% means that none of the beetle larvae have been killed.

  In this test, for example, the following Preparation Example compounds show an effectiveness of 80% or more at a spraying amount of 500 g / ha. I-1-a-1, I-1-a-2, I-1-a-6, I-1-a-9, I-1-a-10, I-1-a-13, I- 1-a-16, I-1-a-17, I-1-a-18, I-1-b-5, I-1-c-4, I-1-c-5, I-1- c-6, I-1-c-10, I-1-c-13, I-1-c-14, I-1-c-15, I-1-c-16, I-1-c- 17, I-1-c-20.

Mizus test (MYZUPE spray treatment)
Solvent: 78 parts by weight of acetone 1.5 parts by weight of dimethylformamide Emulsifier: 0.5 parts by weight of alkylaryl polyglycol ether In order to produce a suitable preparation of the active compound, 1 part by weight of active compound is added in the amount of solvent described. And mixed with emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.

  The discs of Chinese cabbage (Brassica pechinensis) infested with all stages of the green aphid (Myzus persicae) are sprayed with the active compound preparation of the desired concentration.

  After the desired period, the effect is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.

  In this test, for example, the following Preparation Example compounds show an effectiveness of 80% or more at an application rate of 500 g / ha. I-1-a-1, I-1-a-2, I-1-a-3, I-1-a-6, I-1-a-7, I-1-a-9, I- 1-a-10, I-1-a-11, I-1-a-12, J-1-a-13, I-1-a-15, I-1-a-16, I-1- a-17, I-1-a-18, I-1-a-19, I-1-a-21, I-1-a-22, I-1-a-24, I-1-a- 25, I-1-a-26, I-1-b-1, I-1-b-2, I-1-b-5, Ilc-2, I-1-c-3, I-1-c-4, I-1-c-5, I-1-c-6, I-1-c-8, I-1-c-14, I-1-c-15, I- 1-c-16, I-1-c-17, I-1-c-19, I-1-c-20, I-1-c-22, I-1-c-23, I-1- c-24, I-1-c- 5, I-1-c-26, I-1-c-27, I-1-c-28, I-1-c-29.

Spodoptera frugiperda test (SPODFR spray treatment)
Solvent: 78 parts by weight of acetone 1.5 parts by weight of dimethylformamide Emulsifier: 0.5 parts by weight of alkylaryl polyglycol ether In order to produce a suitable preparation of the active compound, 1 part by weight of active compound is added in the amount of solvent described. And mixed with emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.

  A disc of corn leaves (Zea mays) is sprayed with the active compound preparation of the desired concentration, dried and then loaded with worms of Spodoptera frugiperda.

  After the desired period, the effect is determined in%. 100% means that all the worms have been killed; 0% means that none of the worms have been killed.

  In this test, for example, the following Preparation Example compounds show an effectiveness of 80% or more at a spraying amount of 500 g / ha. I-1-a-1, I-1-a-10, I-1-a-11, I-1-a-16, I-1-a-25, I-1-a-26, I- 1-b-5, I-1-c-6, I-1-c-15, I-1-c-16, I-1-c-20.

Tetranics test; OP resistance (TETRUR spray treatment)
Solvent: 7 parts by weight of dimethylformamide Emulsifier: 2 parts by weight of alkylaryl polyglycol ether To produce a suitable preparation of the active compound, 1 part by weight of active compound is mixed with the amount of solvent and emulsifier described and concentrated. Is diluted with emulsifier-containing water to the desired concentration.

  The desired concentration of active compound preparation is sprayed onto the disks of bean leaves (Phaseolus vulgaris) infested with all stages of the greenhouse rat urticae (Tetranychus urticae).

  After the desired period, the effect is determined in%. 100% means that all ticks have died; 0% means that none of the ticks have died.

  In this test, for example, the following Preparation Example compounds show an effectiveness of 80% or more at a spraying rate of 100 g / ha. I-1-a-10, I-1-a-21, I-1-a-22, I-1-a-24, I-1-a-25, I-1-a-26, I- 1-b-1, I-1-b-4, I-1-b-5, I-1-c-3, I-1-c-4, I-1-c-5, I-1- c-13, I-1-c-14, I-1-c-15, I-1-c-16, I-1-c-20, I-1-c-21, I-1-c- 22, I-1-c-23, I-1-c-24, I-1-c-25, I-1-c-26, I-1-c-27, I-1-c-28, I-1-c-29.

Preemergence herbicidal action Monocotyledonous and dicotyledonous weeds and crop seeds are planted in sandy loam soil in a wood fiber pot and covered with soil. The test compound formulated in the form of wettable powder (WP) or emulsion concentrate (EC) is then added as an aqueous suspension with a water application rate of 800 l / ha and 0.2% wetting agent added to the surface of the soil covering. To spray.

  After treatment, the pot is placed in a greenhouse and maintained under good growth conditions for the test plant. After a 3-week trial period, a visual assessment of the damage of the test plants is made by comparison with an untreated control (herbicidal activity in percent (%): 100% activity = plant dead, 0% activity = Same as control plant).

  320 g of a. i. When sprayed by the pre-emergence method at / ha, the following compounds show an efficacy of 80% or more against Lolium multiflorum and Setaria viridis. I-1-a-2, I-1-a-8.

  320 g of a. i. When sprayed by the pre-emergence method at / ha, the following compounds show an efficacy of 80% or more against Lorium multiflorum and Echinohcloa crus-gali. I-1-a-2, I-1-a-3, I-1-a-5, I-1-a-6, I-1-a-7, I-1-a-10, I- 1-a-11, I-1-a-12, I-1-a-19, I-1-a-20, I-1-b-2, I-1-b-3, I-1- b-4, I-1-c-1, I-1-c-2, I-1-c-3, I-1-c-7, I-1-c-9, I-1-c- 10, I-1-c-11, I-1-c-15, I-1-c-16, I-1-c-18, I-1-c-20.

Postemergence herbicidal action Monocotyledonous and dicotyledonous weeds and crop seeds are planted in sandy loam soil in pots of wood fiber, covered with soil, and cultivated in a greenhouse under conditions favorable to growth. Two to three weeks after sowing, the test plants are treated in the single leaf stage. The test compound formulated in the form of wettable powder (WP) or emulsion concentrate (EC) is then added to the plant as an aqueous suspension by adding 0.2% wetting agent at a water application rate of 800 l / ha. Spray the green part of the. After maintaining the test plants in a greenhouse for about 3 weeks under optimal growth conditions, the activity of the preparation is assessed visually in comparison with the treated control (herbicidal activity in percent (%): 100% Activity = plants withered, 0% activity = same as control plants).

  320 g of a. i. When sprayed by the post-emergence method at / ha, the following compounds are more than 80% effective against Avena fatua, Lolium multiflorum, Setaria viridis and Echinochroic crus-galli. I-1-a-2, I-1-a-3, I-1-a-7, I-1-a-8, I-1-a-12, I-1-a-20, I- 1-b-2, I-1-b-3, I-1-c-1, I-1-c-2, I-1-c-11, I-1-c-20.

Postemergence herbicidal action Monocotyledonous and dicotyledonous weeds and crop seeds are planted in sandy loam soil in wood fiber pots or plastic pots, covered with soil, and under good growth conditions, during the growing period Grown in the greenhouse, also outside the greenhouse. Two to three weeks after sowing, the test plants are treated in the single to triple leaf stage. Test compounds formulated in the form of wettable powder (WP) or emulsion concentrate (EC) were added to the wetting agent (0.2 to 0.3%) at various doses with a water application rate of 300 l / ha (converted). ) And spray on plant and soil surfaces. Three to four weeks after treatment of the test plants, the effect of the preparation was assessed visually in comparison with untreated controls (herbicidal activity in percent (%): 100% activity = plants withered, 0 % Activity = similar to control plants).

Use of safeners In the case of crops, if one wishes to further test whether a safener can improve the phytocompatibility of the test substance, the following options are used to use the safener:

The seeds of the crop are dressed with a safener substance before sowing (based on the weight of the seed, the amount of safener is stated in%)
Before use of the test substance, the crop is sprayed with a safener at a certain application rate per hectare (usually one day before use of the test substance).
As a tank mix, a safener is used with the test substance (based on the herbicide, the amount of safener is stated in g / ha or ratio).
By comparing the effects of test substances on crops with and without safener treatments, it is possible to evaluate the effects of safener substances.

Outdoor (“birdcage”) grain container test Mefenpill one day prior to herbicide use

Grain container testing in the greenhouse and outdoors ("birdcage") Mefenpill one day prior to herbicide use

Heliothis virescens test-treatment of transgenic plants Solvent: 7 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether In order to produce a suitable preparation of active compound, 1 part by weight of active compound is described. Is mixed with the amount of solvent and the amount of emulsifier described and the concentrate is diluted with water to the desired concentration.

  Soybean buds (Glycine max) of Round Ready Ready varieties (Monsanto Comp. USA registered trademark) are treated by soaking them in the active compound preparation at the desired concentration, and tobacco moth (Heliotis virescens) while the leaves are wet Was introduced.

  After the desired period, insect death was determined.

Critical Concentration Test / Soil Insect-Treatment of Transgenic Plants Test Insect: Diabrotica balteata-Larvae in Soil Solvent: 7 parts by weight of acetone Emulsifier: 1 part by weight of alkyl aryl polyglycol ether Suitable preparation of active compound In order to produce a product, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

  The active compound preparation is poured into the soil. Here, the active compound concentration in the preparation is substantially irrelevant; only the weight of active compound per unit of soil volume (described in ppm (mg / l)) is important. Pack the soil in a 0.25 liter pot and leave at 20 ° C.

  Immediately after preparation, pre-germinated corn of the YIELD GUARD variety (registered trademark of Monsanto Comp., USA) is sown in each pot. After 2 days, the appropriate test insects are released into the treated soil. After 7 days, the germinated corn plants are counted to determine the effectiveness of the active compound (1 strain = 20% activity).

Claims (26)

The following formula (I)

Wherein W represents hydrogen, alkyl, alkenyl, alkynyl, halogen, alkoxy, haloalkyl, haloalkoxy or cyano,
X represents halogen, alkyl, alkenyl, alkynyl, alkoxy, alkoxyalkoxy, haloalkyl, haloalkoxy or cyano,
Y represents hydrogen, halogen, alkyl, alkenyl, alkynyl, alkoxy, cyano, haloalkyl, haloalkoxy, each optionally substituted phenyl or hetaryl;
Z represents hydrogen, halogen, alkyl, haloalkyl, cyano, alkoxy, or haloalkoxy,
A represents an optionally substituted alkanediyl group or cycloalkyl (optionally substituted and / or optionally interrupted with a heteroatom);
B represents hydrogen or optionally substituted alkyl, alkenyl, alkoxy, alkoxyalkoxy, phenyl, hetaryl, respectively, or cycloalkyl (heteroatom and / or optionally substituted and / or optionally interrupted with C═O) Represents)
Or A represents a bond and B represents hydrogen;
D represents NH or oxygen,
Q ¹ represents hydrogen, each optionally substituted alkyl, alkoxy, alkoxyalkyl or alkylthioalkyl, each optionally substituted cycloalkyl (optionally one methylene group is replaced by a heteroatom). Represents, or optionally substituted phenyl, hetaryl, phenylalkyl or hetarylalkyl;
Q ² represents hydrogen or alkyl,
Q ¹ and Q ² together with the carbon to which they are attached represent an optionally substituted C ₃ -C ₆ -ring (optionally interrupted by a heteroatom), or Q ¹ and Q ² together with the carbon atom to which they are attached represents an optionally substituted C ₃ -C ₆ -ring (optionally interrupted by a heteroatom);
G represents hydrogen (a), and represents one of the following groups:

E represents a metal ion or an ammonium ion;
L represents oxygen or sulfur;
M represents oxygen or sulfur,
R ¹ represents alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl or polyalkoxyalkyl, each optionally substituted with halogen or cyano, or each represents cycloalkyl or heterocyclyl optionally substituted with halogen, alkyl or alkoxy, or Each represents optionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl;
R ² represents alkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl, each optionally substituted with halogen or cyano, or each independently represents cycloalkyl, phenyl or benzyl,
R ³ , R ⁴ and R ⁵ independently of one another each represent optionally halogenated alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio or cycloalkylthio, or each optionally substituted phenyl Represents benzyl, phenoxy or phenylthio,
R ⁶ and R ⁷ independently of one another represent hydrogen and each represents alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl optionally substituted with halogen or cyano, each independently substituted phenyl or benzyl Together with the N atoms to which they are attached, form an optionally substituted ring (optionally containing oxygen or sulfur). )
Compound. W is hydrogen, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, halogen, C ₁ -C ₆ -alkoxy, C ₁ -C ₄ -haloalkyl, C ₁ -C Represents ₄ -haloalkoxy or cyano,
X is _hydrogen, C 1 -C ₆ - _alkyl, C 2 -C ₆ - _alkenyl, C 2 -C ₆ - _alkynyl, C 1 -C ₆ - _alkoxy, C 1 -C ₆ - alkoxy _-C 1 -C ₄ - _alkoxy, C 1 -C ₄ - _haloalkyl, C 1 -C ₄ - haloalkoxy or cyano,
Y is hydrogen, _halogen, C 1 -C ₆ - _alkyl, C 2 -C ₆ - _alkenyl, C 2 -C ₆ - _alkynyl, C 2 -C ₆ - alkoxy, _cyano, C 1 -C ₄ - haloalkyl, halo Represents alkoxy, represents phenyl or pyridyl substituted with V ¹ and V ² ;
V ¹ represents halogen, C ₁ -C ₁₂ -alkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -haloalkoxy, cyano or nitro,
V ² represents hydrogen, halogen, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy or C ₁ -C ₄ -haloalkyl,
V ¹ and V ^{2 taken} together are C ₃ -C ₄ -alkanediyl (optionally substituted with halogen and / or C ₁ -C ₂ -alkyl and one or two oxygen atoms May be interrupted in some cases).
Z is hydrogen, _halogen, C 1 -C ₆ - haloalkoxy, - _alkyl, C 1 -C ₄ - haloalkyl, _cyano, C 1 -C ₆ - alkoxy or _C 1 -C ₄
A optionally is _{C 1 -C 4 - C 1 -C} 4 substituted with alkyl - represents an alkanediyl group or an optionally _{C 1 -C 4, - C 5} -C 8 substituted with an alkyl - cycloalkyl ( Optionally one methylene group is replaced by oxygen).
B represents hydrogen, or C ₁ -C ₈ -alkyl, C ₂ -C ₈ -alkenyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkoxy-C _1- , each optionally substituted with halogen. C ₄ - _alkoxy, C 1 -C ₄ - alkoxy - bis _-C 1 -C ₄ - alkoxy, optionally substituted by halogen, C1-C6- alkyl, C1-C6- alkoxy, C1-C4- haloalkyl, C1-C4 -Represents phenyl substituted with haloalkoxy, cyano or nitro and represents pyridyl, pyrimidyl, thiazolyl or thienyl optionally substituted with halogen, C1-C4-alkyl, or C1-C2-haloalkyl, or optionally halogen , C1-C4-alkyl, C1-C4-alkoxy or C1-C2-haloalkyl. Substituted C ₃ -C ₈ -cycloalkyl (optionally one or two non-adjacent methylene groups are replaced by oxygen, two methylene groups are replaced by the group —O—CO—, or three methylene groups The group is substituted with the group -O-CO-O-),
Or A represents a bond and B represents hydrogen;
D represents NH or oxygen,
Q ¹ represents hydrogen or is optionally halogen-substituted C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, C _1- C ₃ -C ₆ -cycloalkyl (optionally one methylene group) representing C ₄ -alkylthio-C ₁ -C ₄ -alkyl or optionally substituted by halogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -alkoxy Is substituted with oxygen), or phenyl, phenyl-C ₁ -C ₂ -alkyl, or hetaryl (each optionally halogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy) , C ₁ -C ₄ -haloalkyl, or C ₁ -C ₄ -haloalkoxy 1 or 2 substituted).
Q ² represents hydrogen or C ₁ -C ₆ -alkyl, or Q ¹ and Q ² together with the carbon to which they are attached, is a C ₃ -C ₆ -ring (optionally fluorine, chlorine, C _1- C ₄ -alkyl, C ₁ -C ₄ -alkoxy or trifluoromethyl, and optionally substituted one of the methylene groups with oxygen, or Q ¹ And Q ² together with the carbon atom to which they are attached, a C ₃ -C ₆ -ring (optionally fluorine, chlorine, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy or trifluoro 1 or 2 substituted with methyl, and optionally one methylene group may be substituted with oxygen)
G preferably represents hydrogen (a) or represents one of the following groups:

E represents a metal ion or an ammonium ion;
L represents oxygen or sulfur, and M represents oxygen or sulfur,
R ¹ is C ₁ -C ₂₀ -alkyl, C ₂ -C ₂₀ -alkenyl, C ₁ -C ₈ -alkoxy-C ₁ -C ₈ -alkyl, C ₁ -C ₈ , each optionally substituted with halogen or cyano. -Alkylthio-C ₁ -C ₈ -alkyl or poly-C ₁ -C ₈ -alkoxy-C ₁ -C ₈ -alkyl, or optionally substituted by halogen, C1-C6-alkyl or C1-C6-alkoxy C ₃ -C ₈ -cycloalkyl (optionally one or two non-adjacent methylene groups are replaced by oxygen and / or sulfur);
Phenyl optionally substituted with halogen, cyano, nitro, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkyl, C1-C6-haloalkoxy, C1-C6-alkylthio or C1-C6-alkylsulfonyl Represents
Optionally halogen, nitro, cyano, C1-C6- alkyl, C1-C6- alkoxy, C1-C6- haloalkyl or C1-C6- phenyl _-C 1 -C substituted with a haloalkoxy ₆ - alkyl,
Represents a 5- or 6-membered hetaryl having 1 or 2 heteroatoms from the group consisting of oxygen, sulfur, and nitrogen, optionally substituted with halogen or C1-C6-alkyl;
Represents phenoxy-C ₁ -C ₆ -alkyl optionally substituted with halogen or C ₁ -C ₆ -alkyl, or consists of oxygen, sulfur, and nitrogen optionally substituted with halogen, amino or C ₁ -C ₆ -alkyl Represents a 5- or 6-membered hetaryloxy-C ₁ -C ₆ -alkyl having 1 or 2 heteroatoms from the group;
R ² is C ₁ -C ₂₀ -alkyl, C ₂ -C ₂₀ -alkenyl, C ₁ -C ₈ -alkoxy-C ₂ -C ₈ -alkyl or poly-C _1-, each optionally substituted with halogen or cyano. C ₈ - alkoxy _-C 2 -C ₈ - alkyl,
Optionally halogen, C1-C6- alkyl or C1-C6- alkoxy _C 3 substituted by -C ₈ - halogens cycloalkyl and represent, or each, cyano, nitro, C1-C6- alkyl, C1-C6- Represents phenyl or benzyl substituted with alkoxy, C1-C6-haloalkyl or C1-C6-haloalkoxy,
R ³ is C ₁ -C ₈ -alkyl optionally substituted with halogen, or optionally halogen, C1-C6-alkyl, C1-C6-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy, cyano, respectively. Or phenyl or benzyl substituted with nitro,
R ⁴ and R ⁵ are each independently of each other C ₁ -C ₈ -alkyl, C ₁ -C ₈ -alkoxy, C ₁ -C ₈ -alkylamino, di- (C ₁₎ optionally substituted with halogen. -C ₈ - alkyl) _amino, C 1 -C ₈ - alkylthio or _C 3 -C ₈ - represents alkenylthio or optionally substituted by halogen, respectively, nitro, cyano, C1-C4- alkoxy, C1-C4- haloalkoxy, Represents phenyl, phenoxy or phenylthio substituted with C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkyl or C1-C4-haloalkyl;
R ⁶ and R ⁷ independently of one another represent hydrogen, each of C ₁ -C ₈ -alkyl, C ₃ -C ₈ -cycloalkyl, C ₁ -C ₈ -alkoxy optionally substituted with halogen or cyano. , C ₃ -C ₈ -alkenyl or C ₁ -C ₈ -alkoxy-C ₂ -C ₈ -alkyl, each optionally in halogen, C1-C8-alkyl, C1-C8-haloalkyl or C1-C8-alkoxy represents a substituted phenyl or benzyl, or together, when C ₁ -C 6 by _- C ₃ -C 6 substituted with an alkyl _- one methylene group by an alkylene group (if is replaced by oxygen or sulfur Represents)
A compound of formula (I) according to claim 1. W is hydrogen, chlorine, bromine, _iodine, C 1 -C ₄ - _alkyl, C 2 -C ₄ - _alkenyl, C 2 -C ₄ - _alkynyl, C 1 -C ₄ - _alkoxy, C 1 -C ₂ - haloalkyl or Represents C ₁ -C ₂ -haloalkoxy,
X is chlorine, bromine, _iodine, C 1 -C ₄ - _alkyl, C 2 -C ₄ - _alkenyl, C 2 -C ₄ - _alkynyl, C 1 -C ₄ - _alkoxy, C 1 -C ₄ - alkoxy -C ₁ -C ₃ - _alkoxy, C 1 -C ₂ - _haloalkyl, C 1 -C ₂ - haloalkoxy or cyano,
Y is 4-position and represents hydrogen, fluorine, chlorine, bromine, iodine, methoxy, ethoxy, cyano, trifluoromethyl, difluoromethoxy or trifluoromethoxy;
Z represents hydrogen;
W represents hydrogen, chlorine, bromine or C ₁ -C ₄ -alkyl;
X is chlorine, _bromine, C 1 -C ₄ - haloalkoxy or cyano, - _alkyl, C 1 -C ₄ - _alkoxy, C 1 -C ₂ - _haloalkyl, C 1 -C ₂
Y is at the 4 _position, C 2 -C ₄ - _alkenyl, C 2 -C ₄ - an alkynyl, or the group

Represents
Z represents hydrogen,
V ¹ represents fluorine, chlorine, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₂ -haloalkyl or C ₁ -C ₂ -haloalkoxy,
V ² represents hydrogen, fluorine, chlorine, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy or C ₁ -C ₂ -haloalkyl,
V ¹ and V ² together represent —O—CH ₂ —O— and —O—CF ₂ —O—;
W represents hydrogen, chlorine, bromine or C ₁ -C ₄ -alkyl;
X is chlorine, _bromine, C 1 -C ₄ - haloalkyl, - alkyl or _C 1 -C ₂
Y is at the _5-position, C 2 -C ₄ - _alkenyl, C 2 -C ₄ - alkynyl, group

Represents
Z is 4-position and represents hydrogen, C ₁ -C ₄ -alkyl or chlorine;
V ¹ represents fluorine, chlorine, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₂ -haloalkyl or C ₁ -C ₂ -haloalkoxy,
V ² represents hydrogen, fluorine, chlorine, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy or C ₁ -C ₂ -haloalkyl,
V ¹ and V ² together represent —O—CH ₂ —O— or —O—CF ₂ —O—;
W represents hydrogen, C ₁ -C ₄ -alkyl, C ₂ -C ₄ -alkenyl, C ₂ -C ₄ -alkynyl, C ₁ -C ₄ -alkoxy, chlorine, bromine, iodine or trifluoromethyl;
X is chlorine, bromine, _iodine, C 1 -C ₄ - _alkyl, C 2 -C ₄ - _alkenyl, C 2 -C ₄ - _alkynyl, C 1 -C ₄ - _alkoxy, C 1 -C ₄ - alkoxy -C ₁ -C ₃ - _alkoxy, C 1 -C ₂ - _haloalkyl, C 1 -C ₂ - haloalkoxy or cyano,
Y is _4-position, C 1 -C ₄ - alkyl,
Z represents hydrogen;
W is hydrogen, chlorine, bromine, _iodine, C 1 -C ₄ - alkoxy, - alkyl or _C 1 -C ₄
X is chlorine, bromine, _iodine, C 1 -C ₄ - haloalkoxy or cyano, - _alkyl, C 1 -C ₄ - _alkoxy, C 1 -C ₂ - _haloalkyl, C 1 -C ₂
Y is 4-position, hydrogen, chlorine, _bromine, C 1 -C ₄ - haloalkoxy, - _alkyl, C 1 -C ₂ - haloalkyl or _C 1 -C ₂
Z is 3-position or 5-position, and fluorine, chlorine, bromine, iodine, C ₁ -C ₄ -alkyl, C ₁ -C ₂ -haloalkyl, C ₁ -C ₄ -alkoxy or C ₁ -C ₂ -haloalkoxy Representation;
A represents a C ₁ -C ₃ -alkanediyl group optionally substituted with C ₁ -C ₂ -alkyl, or C ₅ -C ₆ -cycloalkyl (optionally one methylene group is replaced by oxygen. );
B is hydrogen or _C 1 -C ₆ - _alkyl, C 2 -C ₆ - _alkenyl, C 1 -C ₄ - _alkoxy, C 1 -C ₄ - alkoxy _-C 1 -C ₃ - _alkoxy, C 1 -C ₄ - Represents alkoxy-bis-C ₁ -C ₃ -alkoxy (each optionally substituted by 1 to 3 with fluorine or chlorine) phenyl (optionally fluorine, chlorine, bromine, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₂ -haloalkyl, C ₁ -C ₂ -haloalkoxy, cyano or nitro substituted 1-3), and represents pyridyl, pyrimidyl, thiazolyl or thienyl (respectively, optionally fluorine, chlorine, bromine, methyl, ethyl or is 1 or 2 substituted by trifluoromethyl), or _C 3 -C ₆ -. cycloalkyl (Optionally fluorine, chlorine, methyl, methoxy, or is 1 or 2 substituted by trifluoromethyl,. Two methylene groups not adjacent one or directly are replaced by oxygen optionally) represents,
Or A represents a bond and B represents hydrogen;
D represents NH or oxygen;
Q ¹ represents hydrogen and represents C ₁ -C ₄ -alkyl (optionally substituted by 1 to 3 with fluorine);
Q ² represents hydrogen or C ₁ -C ₄ -alkyl;
Q ¹ and Q ² together with the carbon atom to which they are attached are optionally substituted with a C ₃ -C ₆ -ring (optionally substituted with fluorine, methyl, methoxy, or trifluoromethyl, and optionally one Methylene group may be substituted with oxygen), or Q ¹ and Q ² together with the carbon atom to which they are attached, is a C ₃ -C ₆ -ring (optionally fluorine, methyl, 1 substituted with methoxy or trifluoromethyl, and optionally one methylene group may be substituted with oxygen);
G represents hydrogen (a) or one of the following groups;

E represents a metal ion or an ammonium ion;
L represents oxygen or sulfur, and M represents oxygen or sulfur,
R ¹ is C ₁ -C ₁₆ -alkyl, C ₂ -C ₁₆ -alkenyl, C ₁ -C ₆ -alkoxy-C ₁ -C ₄ -alkyl, C ₁ -C ₆ -alkylthio-C ₁ -C ₄ -alkyl. Or represents poly-C ₁ -C ₆ -alkoxy-C ₁ -C ₄ -alkyl (each optionally substituted by 1 to 3 with fluorine or chlorine), or C ₃ -C ₇ -cycloalkyl (optional) 1 to 2 substituted with fluorine, chlorine, C ₁ -C ₅ -alkyl or C ₁ -C ₅ -alkoxy, and optionally one or two non-adjacent methylene groups are replaced with oxygen and / or sulfur .)
Phenyl (optionally fluorine, chlorine, bromine, cyano, _nitro, C 1 -C ₄ - _alkyl, C 1 -C ₄ - _alkoxy, C 1 -C ₃ - _haloalkyl, C 1 -C ₃ - haloalkoxy, _{C 1} - C ₄ - alkylthio or _C 1 -C ₄ -. is 1 to 3 substituted alkylsulfonyl) represents,
Phenyl-C ₁ -C ₄ -alkyl (optionally fluorine, chlorine, bromine, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₃ -haloalkyl or C ₁ -C ₃ -haloalkoxy And 1 to 2 substitutions).
Represents pyrazolyl, thiazolyl, pyridyl, pyrimidinyl, furanyl or thienyl (each optionally substituted 1 to 2 with fluorine, chlorine, bromine or C ₁ -C ₄ -alkyl).
Represents phenoxy-C ₁ -C ₅ -alkyl (optionally substituted by 1 to 2 with fluorine, chlorine, bromine or C ₁ -C ₄ -alkyl), or pyridyloxy-C ₁ -C ₅ -alkyl, pyrimidyloxy -C ₁ -C ₅ -alkyl or thiazolyloxy-C ₁ -C ₅ -alkyl, each optionally substituted by 1 to 2 with fluorine, chlorine, bromine, amino or C ₁ -C ₄ -alkyl.
R ² is C ₁ -C ₁₆ -alkyl, C ₂ -C ₁₆ -alkenyl, C ₁ -C ₆ -alkoxy-C ₂ -C ₆ -alkyl or poly-C ₁ -C ₆ -alkoxy-C ₂ -C. Represents ₆ -alkyl, each optionally substituted by 1 to 3 with fluorine or chlorine,
C ₃ -C ₇ -cycloalkyl (optionally substituted by 1 to 2 with fluorine, chlorine, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -alkoxy), or phenyl or benzyl (respectively optionally fluorine, chlorine, bromine, cyano, _nitro, C 1 -C ₄ - _alkyl, C 1 -C ₃ - _alkoxy, C 1 -C ₃ - haloalkyl, or _C 1 -C ₃ - is from 1 haloalkoxy trisubstituted ),
R ³ represents C ₁ -C ₆ -alkyl (optionally substituted with 1 to 3 by fluorine or chlorine) or phenyl or benzyl (respectively optionally fluorine, chlorine, bromine, C ₁ -C ₄ - _alkyl, C 1 -C ₄ - _alkoxy, C 1 -C ₂ - _haloalkoxy, C 1 -C ₂ - haloalkyl, 2-substituted 1 cyano or nitro).
R ⁴ and R ⁵ are independently of each other C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkylamino, di- (C ₁ -C ₆ -alkyl) amino, C ₁ -C ₆ -alkylthio or C ₃ -C ₄ -alkenylthio (respectively optionally substituted by 1 to 3 with fluorine or chlorine), or phenyl, phenoxy or phenylthio (respectively optionally fluorine, chlorine, bromine, nitro, _cyano, C 1 -C ₃ - _alkoxy, C 1 -C ₃ - _haloalkoxy, C 1 -C ₃ - _alkylthio, C 1 -C ₃ - _{haloalkylthio,} C 1 -C ₃ - alkyl or 1 to 2 substituted with C ₁ -C ₃ -haloalkyl).
R ⁶ and R ⁷ independently of one another represent hydrogen and are C ₁ -C ₆ -alkyl, C ₃ -C ₆ -cycloalkyl, C ₁ -C ₆ -alkoxy, C ₃ -C ₆ -alkenyl or C _1- C ₆ -alkoxy-C ₂ -C ₆ -alkyl (respectively optionally substituted by 1 to 3 with fluorine or chlorine), phenyl or benzyl (respectively optionally fluorine, chlorine, bromine, C ₁ -C ₅ -haloalkyl, C ₁ -C ₅ -alkyl or C ₁ -C ₅ -alkoxy is substituted by 1 to 3), or together, optionally substituted by C ₁ -C ₄ -alkyl Or a C ₃ -C ₆ -alkylene group (optionally one methylene group is replaced by oxygen or sulfur),
A compound of formula (I) according to claim 1. W particularly preferably represents hydrogen, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy or trifluoromethyl;
X particularly preferably represents chlorine, bromine, iodine, methyl, ethyl, propyl, methoxy, ethoxy, propoxy, methoxyethoxy, ethoxyethoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy or cyano,
Y is in the 4-position, more particularly preferably represents hydrogen, chlorine, bromine, iodine, trifluoromethyl or trifluoromethoxy;
Z particularly preferably represents hydrogen;
W also more particularly preferably represents hydrogen, chlorine, bromine, methyl or ethyl,
X also more particularly preferably represents chlorine, bromine, methyl, ethyl, propyl, methoxy, trifluoromethyl, difluoromethoxy or cyano,
Y also more particularly preferably represents vinyl, ethynyl, propynyl in the 4-position, or a group

Represents
Z also more particularly preferably represents hydrogen,
V ¹ also more particularly preferably represents fluorine, chlorine, methyl, methoxy, trifluoromethyl or trifluoromethoxy,
V ² also more particularly preferably represents hydrogen, fluorine, chlorine, methyl, methoxy or trifluoromethyl;
W likewise likewise particularly preferably represents hydrogen, chlorine or methyl,
X likewise likewise more preferably represents chlorine, methyl or trifluoromethyl,
Y likewise likewise particularly preferably represents the vinyl, ethynyl, propynyl at the 5 position or the group

Represents
Z likewise represents hydrogen or methyl at the 4-position,
V ¹ likewise represents fluorine, chlorine, methyl, methoxy, methoxy, or trifluoromethyl or trifluoromethoxy,
V ² likewise represents hydrogen, fluorine, chlorine, methyl, trifluoromethyl;
W represents still further hydrogen, methyl, ethyl, methoxy, ethoxy, chlorine, bromine or iodine;
X still further represents chlorine, bromine, iodine, methyl, ethyl, propyl, methoxy, ethoxy, propoxy, methoxyethoxy, ethoxyethoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy or cyano;
Y still further represents methyl or ethyl at the 4-position;
Z still further represents hydrogen;
W further represents hydrogen, chlorine, bromine, iodine, methyl or ethyl,
X further represents chlorine, bromine, iodine, methyl, ethyl, methoxy, trifluoromethyl, difluoromethoxy or trifluoromethoxy,
Y further represents hydrogen, chlorine, bromine, iodine, methyl or ethyl at the 4-position;
Z further represents fluorine, chlorine, bromine, iodine, methyl, ethyl, trifluoromethyl or trifluoromethoxy at the 3- or 5-position;
A is _{-CH 2 -, - CHCH 3 -} , - CH 2 -CH 2 -, - CH 2 -CHCH 3 -, - CH 2 -CH 2 -CH 2 - represents;
B is hydrogen, methyl, ethyl, propyl, isopropyl, butyl, _isobutyl, C 2 -C ₄ - represents alkenyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, methoxyethoxy, ethoxyethoxy, phenyl (fluorine optionally , Chlorine, bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro, or cyclopropyl, cyclopentyl or cyclohexyl (optionally one methylene group is oxygenated) To be replaced)
Or A more particularly preferably represents a bond and B represents hydrogen;
D represents NH or oxygen;
Q ¹ represents hydrogen, methyl or ethyl;
Q ² represents hydrogen, methyl or ethyl;
Q ¹ and Q ² together with the carbon atom to which they are attached represent cyclopropyl, cyclopentyl, or cyclohexyl, or Q ¹ and Q ² together with the carbon atom to which they are attached, Represents a _5- C ₆ -ring (optionally interrupted by oxygen);
G represents hydrogen (a) or one of the following groups;

E represents a metal ion or an ammonium ion;
L represents oxygen or sulfur, and M represents oxygen or sulfur,
R ¹ is C ₁ -C ₁₀ -alkyl, C ₂ -C ₁₀ -alkenyl, C ₁ -C ₄ -alkoxy-C ₁ -C ₂ -alkyl, C ₁ -C ₄ -alkylthio-C ₁ -C _2- Represents alkyl (each optionally substituted 1 to 3 with fluorine or chlorine) or C ₃ -C ₆ -cycloalkyl (optionally 1 substituted with fluorine, chlorine, methyl, ethyl or methoxy). Represents
Phenyl (optionally substituted by 1 to 2 with fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, trifluoromethyl or trifluoromethoxy);
Represents furanyl, thienyl or pyridyl (in each case optionally substituted by chlorine, bromine or methyl);
R ² represents C ₁ -C ₁₀ -alkyl, C ₂ -C ₁₀ -alkenyl or C ₁ -C ₄ -alkoxy-C ₂ -C ₄ -alkyl (each optionally substituted 1 to 3 with fluorine or chlorine) .)
Represents cyclopentyl or cyclohexyl,
Or represents phenyl or benzyl, each optionally substituted by 1 to 2 with fluorine, chlorine, cyano, nitro, methyl, ethyl, methoxy, trifluoromethyl or trifluoromethoxy.
R ³ represents methyl, ethyl, propyl or isopropyl (optionally substituted by 1 to 3 with fluorine or chlorine, respectively), or phenyl (optionally fluorine, chlorine, bromine, methyl, ethyl, isopropyl, tert-butyl, 1-substituted with methoxy, ethoxy, isopropoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro.
R ⁴ and ^{R 5} independently ^of one _another, C 1 -C ₄ - alkoxy or _C 1 -C ₄ - alkylthio, or phenyl, represents phenoxy or phenylthio (fluorine optionally each chlorine, bromine, nitro , Monosubstituted with cyano, methyl, methoxy, trifluoromethyl or trifluoromethoxy).
R ⁶ and R ⁷ independently of one another represent hydrogen and are C ₁ -C ₄ -alkyl, C ₃ -C ₆ -cycloalkyl, C ₁ -C ₄ -alkoxy, C ₃ -C ₄ -alkenyl or C _1- C ₄ -alkoxy-C ₂ -C ₄ -alkyl, phenyl (optionally substituted 1 to 2 with fluorine, chlorine, bromine, methyl, methoxy or trifluoromethyl) or together C ₅ -C 6 Te _- represents an alkylene group (one methylene group is replaced by oxygen or sulfur optionally.),
A compound of formula (I) according to claim 1. Where
W represents methyl, ethyl or methoxy;
X represents chlorine, methyl, ethyl or methoxy;
Y is 4-position and represents chlorine or bromine;
Z represents hydrogen;
W likewise represents hydrogen,
X likewise represents methyl,
Y is also in the 5-position,

Represents
Z is in position 4 and represents hydrogen;
W still further represents methyl or ethyl;
X still further represents chlorine, bromine or methyl;
Y is still further in position 4 and represents methyl;
Z still further represents hydrogen;
A represents —CH ₂ — or —CH ₂ —CH ₂ —,
B represents hydrogen, methyl, ethyl, propyl, methoxy or cyclopropyl;
Or A represents a bond and B represents hydrogen;
D represents NH;
Q ¹ represents hydrogen;
Q ² particularly preferably represents hydrogen;
G particularly preferably represents hydrogen (a) or one of the following groups:

Where E represents a metal ion,
L represents oxygen, and M represents oxygen,
R ¹ is _C 1 _{-C 10} - alkyl,
Represents phenyl (optionally 1 substituted with chlorine);
R ² represents C ₁ -C ₁₀ -alkyl or C ₂ -C ₁₀ -alkenyl,
R ³ represents methyl,
R ⁶ and R ⁷ together represent a C ₅ -C ₆ -alkylene group (optionally one methylene group is replaced with oxygen);
A compound of formula (I) according to claim 1. A process for the preparation of a compound of formula (I) according to claim 1,
(A) Compound of formula (I-1-a)

(Where
A, B, Q ¹ , Q ² , W, X, Y and Z are as defined above. )
In the presence of a diluent and in the presence of a base,
Compound of formula (II)

(Where
A, B, Q ¹ , Q ² , W, X, Y and Z are as defined above,
R8 represents alkyl. )
Condensing in the molecule,
(B) Compound of formula (I-2-a)

(Where
A, B, Q ¹ , Q ² , W, X, Y and Z are as defined above. )
In the presence of a diluent and in the presence of a base,
Compound of formula (III)

(Where
A, B, Q ¹ , Q ² , W, X, Y, Z and R ⁸ are as defined above. ()
Condensing in the molecule,
(C) Compounds of formula (I-1-b) to (I-2-b) above (R ¹ , A, B, Q ¹ , Q ² , W, X, Y and Z are defined above. In order to obtain a compound of formula (I-1-a) to (I-2-a) above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder. ) (A, B, Q ¹ , Q ² , W, X, Y and Z are as defined above), respectively,
α) Compound of formula (IV)

(Where
R ¹ is as defined above,
Hal represents halogen. )
Or β) carboxylic anhydride of formula (V) R ¹ —CO—O—CO—R ¹ (V)
(Where
R ¹ is as defined above. )
React with
(D) The compounds of the above formulas (I-1-c) to (I-2-c) (R ² , A, B, Q ¹ , Q ² , W, M, X, Y and Z are As defined, and L represents oxygen) in order to obtain a compound of formula (I-1-a), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder. ) To (I-2-a) compounds (A, B, Q ¹ , Q ² , W, X, Y and Z are as defined above), respectively, of formula (VI)
^{R 2 -M-CO-Cl (} VI)
Where
(R ² and M are as defined above.)
Reacting with chloroformate or chloroformate thioester of
(E) Compounds of formulas (I-1-c) to (I-2-c) above (R ² , A, B, Q ¹ , Q ² , W, M, X, Y and Z are As defined, and L represents sulfur) in the presence of a diluent, if appropriate, and in the presence of an acid binder, if appropriate, of formula (I-1-a ) To (I-2-a) compounds (A, B, Q ¹ , Q ² , W, X, Y and Z are as defined above), respectively, of formula (VII)

(Where
M and R ² are as defined above. )
Reacting with chloromonothioformate or chlorodithioformate,
(F) Compounds of formulas (I-1-d) to (I-2-d) above (R ³ , A, B, W, Q ¹ , Q ² , X, Y and Z are defined above. In order to obtain a compound of formula (I-1-a) to (I-2-a) above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder. ) Of the formula (A, B, Q ¹ , Q ² , W, X, Y and Z are as defined above), each of formula (VIII)
R ³ —SO ₂ —Cl (VIII)
(Where
R ³ is as defined above. )
(G) Compounds (L, R ⁴ , R ⁵ , A, B, Q ¹ , Q ² , W) of the above formulas (I-1-e) to (I-2-e) , X, Y and Z are as defined above) in the presence of a diluent, if appropriate, and in the presence of an acid binder, if appropriate. -1-a) to (I-2-a) compounds (A, B, Q ¹ , Q ² , W, X, Y and Z are as defined above) are each represented by the formula (IX)

(Where
L, R ⁴ and R ⁵ are as defined above,
Hal represents halogen. )
Reacting with a phosphorus compound of
(H) Compounds of formula (I-1-f) to (I-2-f) above (E, A, B, Q ¹ , Q ² , W, X, Y and Z are defined above. To obtain the compounds (A, B, Q ¹ , Q ² ) of formulas (I-1-a) to (I-2-a) above, if appropriate in the presence of a diluent. , W, X, Y and Z are as defined above.) In the respective formulas (X) and (XI)

(Where
Me represents a monovalent or divalent metal,
t represents a numerical value of 1 or 2, and R ¹⁰ , R ¹¹ and R ¹² each independently represent hydrogen or alkyl. )
(I) Compound (L, R ⁶ , R ⁷ , A, B, Q ¹ , Q ² ) of the above formulas (I-1-g) to (I-2-g) , W, X, Y and Z are as defined above.) To obtain the compounds of formulas (I-1-a) to (I-2-a) (A, B, Q ¹ , Q ² , W, X, Y and Z are as defined above), respectively,
α) if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst of formula (XII)
^{R 6 -N = C = L (} XII)
(Where
R ⁶ and L are as defined above. )
Or β) in the presence of a diluent, if appropriate, and in the presence of an acid binder, if appropriate, of the formula (XIII)

(Where
L, R ⁶ and R ⁷ are as defined above. )
Reacting with carbamoyl chloride or thiocarbamoyl chloride of
Characterized by the process. As a component,
(A ′) at least one compound of formula (I) (A, B, D, G, Q ¹ , Q ² , W, X, Y and Z are as defined above), and (B ′) at least one crop suitability improving compound from the group of the following compounds:
4-dichloroacetyl-1-oxa-4-azaspiro [4.5] decane (AD-67, MON-4660), 1-dichloroacetylhexahydro-3,3,8a-trimethylpyrrolo [1,2-a] Pyrimidin-6 (2H) -one (dicyclonon, BAS-145138), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (benoxacol) 1-methylhexyl 5-chloroquinoline-8-oxyacetate (cloquintocet-mexyl-note, EP-A-86750, EP-A-94349, EP-A-191736, EP-A -492366 also related compounds), 3- (2-chlorobenzyl) -1- (1 -Methyl-1-phenylethyl) urea (cumyluron), α- (cyanomethoxyimino) phenylacetonitrile (cyometrinil), 2,4-dichlorophenoxyacetic acid (2,4-D), 4- ( 2,4-dichlorophenoxy) butyric acid (2,4-DB), 1- (1-methyl-1-phenylethyl) -3- (4-methylphenyl) urea (Daimuron, dymron), 3,6 -Dichloro-2-methoxybenzoic acid (dicamba), S-1-methyl-1-phenylethylpiperidine-1-thiocarboxylate (dimipeperate), 2,2-dichloro-N- (2- Oxo-2- (2-propenylamino) ethyl) -N- (2-pro Nyl) acetamide (DKA-24), 2,2-dichloro-N, N-di-2-propenylacetamide (dichloromid), 4,6-dichloro-2-phenylpyrimidine (fenchlorim), ethyl 1- (2,4-Dichlorophenyl) -5-trichloromethyl-1H-1,2,4-triazole-3-carboxylate (fenchlorazole-ethyl-note, EP-A-174562 and EP-A -346620 and related compounds), phenylmethyl 2-chloro-4-trifluoromethylthiazole-5-carboxylate (flurazole), 4-chloro-N- (1,3-dioxolan-2-ylmethoxy)- α-trifluoroacetofu Nonoxime (fluxofenim), 3-dichloroacetyl-5- (2-furanyl) -2,2-dimethyloxazolidine (furilazole, MON-13900), ethyl 4,5-dihydro-5,5-diphenyl -3-Ixazolecarboxylate (Ioxadifen-ethyl-note, related compound also to WO-A-95 / 07897), 1- (ethoxycarbonyl) ethyl 3,6-dichloro-2-methoxybenzoate (lactide dichloro) (Lactide dichlor)), (4-chloro-o-toluyloxy) acetic acid (MCPA), 2- (4-chloro-o-toluyloxy) propionic acid (mecoprop), diethyl 1- (2,4-dichloro Enyl) -4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl-note, also a compound related to WO-A-91 / 07874), 2-dichloro Methyl-2-methyl-1,3-dioxolane (MG-191), 2-propenyl-1-oxa-4-azaspiro [4.5] decan-4-carbodithioate (MG-838), anhydrous 1,8 -Naphthalic acid, α- (1,3-dioxolan-2-ylmethoxyimino) phenylacetonitrile (oxabetrilin), 2,2-dichloro-N- (1,3-dioxolan-2-ylmethyl) -N— (2-propenyl) acetamide (PPG-1292), 3-dichloroacetyl-2,2-dimethyloxazolidine R-28725), 3-dichloroacetyl-2,2,5-trimethyloxazolidine (R-29148), 4- (4-chloro-o-toluyl) butyric acid, 4- (4-chlorophenoxy) butyric acid, diphenylmethoxyacetic acid Methyldiphenylmethoxyacetate, ethyldiphenylmethoxyacetate, methyl 1- (2-chlorophenyl) -5-phenyl-1H-pyrazole-3-carboxylate, ethyl 1- (2,4-dichlorophenyl) -5-methyl- 1H-pyrazole-3-carboxylate, ethyl 1- (2,4-dichlorophenyl) -5-isopropyl-1H-pyrazole-3-carboxylate, ethyl 1- (2,4-dichlorophenyl) -5- (1,1 -Dimethylethyl) -1H-pyrazole-3-carboxylate, ethyl 1- 2,4-dichlorophenyl) -5-phenyl-1H-pyrazole-3-carboxylate (note, also related to EP-A-269806 and EP-A-333131), ethyl 5- (2,4-dichlorobenzyl) 2-Ixazoline-3-carboxylate, ethyl 5-phenyl-2-ixazoline-3-carboxylate, ethyl 5- (4-fluorophenyl) -5-phenyl-2-oxazoline-3-carboxylate ( Note, WO-A-91 / 08202 is also a related compound), 1,3-dimethylbut-1-yl 5-chloroquinoline-8-oxyacetate, 4-allyloxybutyl 5-chloroquinoline-8-oxyacetate Tart, 1-allyloxyprop-2-yl 5-chloroquinoline-8-oxyacetate, methyl 5-methyl Loquinoxaline-8-oxyacetate, ethyl 5-chloroquinoline-8-oxyacetate, allyl 5-chloroquinoxaline-8-oxyacetate, 2-oxoprop-1-yl 5-chloroquinoline-8-oxyacetate Diethyl 5-chloroquinoline-8-oxymalonate, diallyl 5-chloroquinoxaline-8-oxymalonate, diethyl 5-chloroquinoline-8-oxymalonate (note, also related to EP-A-582198), 4-carboxychroman-4-ylacetic acid (AC-304415, Note, EP-A-613618), 4-chlorophenoxyacetic acid, 3,3′-dimethyl-4-methoxybenzophenone, 1-bromo-4-chloromethylsulfonyl Benzene, 1- [4- (N-2-methoxybenzoylsulfamo) L) phenyl] -3-methylurea (also known as N- (2-methoxybenzoyl) -4-[(methylaminocarbonyl) amino] benzenesulfonamide), 1- [4- (N-2-methoxybenzoylsulfate) Famoyl) phenyl] -3,3-dimethylurea, 1- [4- (N-4,5-dimethylbenzoylsulfamoyl) phenyl] -3-methylurea, 1- [4- (N-naphthylsulfa) Moyl) phenyl] -3,3-dimethylurea, N- (2-methoxy-5-methylbenzoyl) -4- (cyclopropylaminocarbonyl) benzenesulfonamide,
And / or the following formula (IIa)

Or formula (IIb)

Or formula (IIc)

(Where
m represents a numerical value of 0, 1, 2, 3, 4 or 5;
A ¹ represents one of the divalent heterocyclic groups shown below,

n represents a numerical value of 0, 1, 2, 3, 4 or 5;
A ² represents alkanediyl having 1 or 2 carbon atoms, optionally substituted with C1-C4-alkyl and / or C1-C4-alkoxycarbonyl and / or C1-C4-alkenyloxycarbonyl;
R ¹⁴ represents hydroxyl, mercapto, amino, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkylthio, C ₁ -C ₆ -alkylamino or di (C ₁ -C ₄ -alkyl) amino;
R ¹⁵ is hydroxyl, mercapto, amino, C ₁ -C ₇ -alkoxy, C ₁ -C ₆ -alkenyloxy, C ₁ -C ₆ -alkenyloxy-C ₁ -C ₆ -alkoxy, C ₁ -C _{6- alkylthio,} C 1 -C ₆ - alkylamino or di _(C 1 -C ₄ - alkyl) - an amino,
R ¹⁶ represents C ₁ -C ₄ -alkyl optionally substituted with fluorine, chlorine and / or bromine;
R ¹⁷ is hydrogen, fluorine, optionally respectively, chlorine and / or _C 1 -C bromine-substituted ₆ - _alkyl, C 2 -C ₆ - alkenyl or _C 2 -C ₆ - _alkynyl, C 1 -C ₄ - Alkoxy-C ₁ -C ₄ -alkyl, dioxolanyl-C ₁ -C ₄ -alkyl, furyl, furyl-C ₁ -C ₄ -alkyl, thienyl, thiazolyl, piperidinyl, or optionally fluorine, chlorine and / or bromine, Or represents phenyl substituted with C ₁ -C ₄ -alkyl,
R ¹⁸ is hydrogen, fluorine, optionally respectively, _C 1 -C substituted by chlorine and / or bromine ₆ - _alkyl, C 2 -C ₆ - alkenyl or _C 2 -C ₆ - _alkynyl, C 1 -C ₄ - Alkoxy-C ₁ -C ₄ -alkyl, dioxolanyl-C ₁ -C ₄ -alkyl, furyl, furyl-C ₁ -C ₄ -alkyl, thienyl, thiazolyl, piperidinyl, or optionally fluorine, chlorine and / or bromine, Or phenyl substituted with C ₁ -C ₄ -alkyl, R ¹⁷ and R ^{18 taken} together represent C ₃ -C ₆ -alkanediyl or C ₂ -C ₅ -oxaalkanediyl (respectively optionally C ₁ -C 4 _- alkyl, phenyl, furyl, substituted with condensed benzene ring, or is substituted with two substituents Two substituents form a 5-membered or 6-membered carbocyclic ring together with the C atom to which they are attached.)
R ¹⁹ represents hydrogen, cyano, halogen, each representing C ₁ -C ₄ -alkyl, C ₃ -C ₆ -cycloalkyl or phenyl optionally substituted with fluorine, chlorine and / or bromine,
R ²⁰ is hydrogen, optionally substituted by hydroxyl, respectively, cyano, _C 1 -C substituted by halogen or C1-C4- alkoxy ₆ - _alkyl, C 3 -C ₆ - cycloalkyl or tri - _(C 1 -C ₄ - Alkyl) -silyl,
R ²¹ represents hydrogen, cyano, halogen, or C ₁ -C ₄ -alkyl, C ₃ -C ₆ -cycloalkyl or phenyl, each optionally substituted with fluorine, chlorine and / or bromine,
X ¹ represents nitro, cyano, halogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -haloalkoxy,
X ² represents hydrogen, cyano, nitro, halogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -haloalkoxy,
X ³ represents hydrogen, cyano, nitro, halogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -haloalkoxy. )
One of the compounds defined by the general formula:
And / or the following formula (IId)

Or formula (IIe)

(Where
t represents a numerical value of 0, 1, 2, 3, 4 or 5;
v represents a numerical value of 0, 1, 2, 3, 4 or 5;
R ²² represents hydrogen or C ₁ -C ₄ -alkyl,
R ²³ represents hydrogen or C ₁ -C ₄ -alkyl,
R ²⁴ is hydrogen, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkylthio, C ₁ -C, each optionally substituted with cyano, halogen or C1-C4-alkoxy. ₆ - alkylamino or di _(C 1 -C ₄ - alkyl) - amino or cyano optionally each halogen or C1-C4- alkyl substituted _C 3 -C ₆ - _cycloalkyl, C 3 -C ₆ - cycloalkyl _alkyloxy, C 3 -C ₆ - cycloalkylthio or _C 3 -C ₆ - cycloalkyl, amino,
R ²⁵ is hydrogen, C ₁ -C ₆ -alkyl optionally substituted with cyano, hydroxyl, halogen or C ₁ -C ₄ -alkoxy, C ₃ -C ₆ -alkenyl optionally substituted with cyano- or halogen, respectively C ₃ -C ₆ - alkynyl _C 3 -C ₆ or optionally substituted cyano, halogen or C1-C4- alkyl, - cycloalkyl,
R ²⁶ is C ₁ -C ₆ -alkyl substituted with hydrogen, optionally cyano, hydroxyl, halogen or C ₁ -C ₄ -alkoxy, C ₃ -C ₆ -alkenyl or C optionally substituted with cyano or halogen, respectively. ₃ -C ₆ - alkynyl, optionally cyano, halogen or C1-C4- alkyl _C 3 substituted by -C ₆ - cycloalkyl or optionally nitro, cyano, halogen, C1-C4- alkyl, C1-C4- haloalkyl , C1-C4- alkoxy or phenyl substituted with C1-C4- haloalkoxy, or together with ^{R 25,} _C 1 -C ₄ each optionally - _C 2 -C ₆ substituted alkyl - alkanediyl or _C 2 -C ₅ - represents oxa alkanediyl,
X ⁴ is nitro, cyano, carboxy, carbamoyl, formyl, sulfamoyl, hydroxyl, amino, halogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy or C ₁ -C Represents ₄ -haloalkoxy, and X ⁵ is nitro, cyano, carboxy, carbamoyl, formyl, sulfamoyl, hydroxyl, amino, halogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C _{It represents 4} -alkoxy or C ₁ -C ₄ -haloalkoxy. )
One of the compounds defined by the general formula:
A composition comprising an effective amount of an active compound combination comprising: Crop compatibility improving compounds include:
Croquintoset mexil, fenchlorazole ethyl, oxadiphenethyl, mefenpyrdiethyl, furirazole, fenchlorin, cumyluron, diimron, or compound

and

8. A composition according to claim 7, characterized in that it is selected from the group of compounds.   9. Composition according to claim 7 or 8, characterized in that the crop compatibility improving compound is croquintoset mexil.   9. Composition according to claim 7 or 8, characterized in that the crop compatibility improving compound is mefenpyrdiethyl. 8. At least one compound of formula (I) according to claim 1 or a composition according to claim 7, and at least one compound of formula (III ')

(Where
D represents nitrogen or phosphorus;
R ²⁶ , R ²⁷ , R ²⁸ and R ²⁹ are independently of one another hydrogen or each optionally substituted C ₁ -C ₈ -alkyl or monounsaturated or polyunsaturated optionally substituted C ₁ -C 8 _- alkylene, the substituents are selected from halogen, nitro, and cyano,
n represents 1, 2, 3 or 4;
R ³⁰ represents an organic anion or an inorganic anion. )
A composition comprising:   12. Composition according to claim 11, characterized in that it comprises at least one penetrant.   Use of a compound of formula (1) according to claim 1 for the preparation of insecticides and / or herbicides and / or fungicides.   Insecticide and / or herbicide and / or fungicide, characterized in that it comprises at least one compound of formula (I) according to claim 1.   Animal pests and / or undesired vegetation and / or fungi, characterized in that the compounds of formula (I) according to claim 1 act on pests and / or their habitats How to control.   Use of a compound of formula (I) according to claim 1 for controlling animal pests and / or undesirable vegetation and / or fungi.   Process for the preparation of insecticides and / or herbicides and / or fungicides, characterized in that the compound of formula (I) according to claim 1 is mixed with bulking agents and / or surfactants.   A method for controlling undesired vegetation, wherein the composition according to claim 7 is allowed to act on a plant or its habitat.   Use of the composition according to claim 7 for controlling undesired vegetation.   The compound of the formula (I) according to claim 1 and the crop compatibility improving compound according to claim 7 are allowed to act separately on a plant or in the vicinity thereof in a short time continuously. How to control unwanted vegetation.   A compound of formula (I) according to claim 1 or a claim 7 characterized in that a ready-to-use composition (spray solution) is prepared using the salt of formula (III ') according to claim 11. A method for improving the activity of an insecticide and / or herbicide comprising the composition described in 1.   The method according to claim 21, characterized in that the spray liquid is prepared with a penetrant. Formula (II)

(Where
A, B, Q ¹ , Q ² , W, X, Y, Z and R ⁸ are as defined above)
Compound. Formula (III)

(Where
A, B, Q ¹ , Q ² , W, X, Y, Z and R ⁸ are as defined above. )
Compound. Formula (XVI)

(Where
A, B, Q ¹ , Q ² , W, X, Y and Z are as defined above. )
Compound. Formula (XVII)

(Where
A, B, Q ¹ , Q ² and R ⁸ are as defined above. )
Compound.